Organic chemistry Books
de Gruyter Neue Ergebnisse Der Polymerforschung
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£134.09
de Gruyter Grundlagen Der Quantitativen Theorie Organischer
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£134.09
de Gruyter Schmelzpunkttabellen Organischer Verbindungen
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£134.09
de Gruyter Methanol Chemie Und Energierohstoff
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£134.09
de Gruyter Chemie Und Technologie Der
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£134.09
de Gruyter Elektroorganische Chemie
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£134.09
de Gruyter Ergebnisse Der AlkaloidChemie Bis 1960
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£141.54
De Gruyter Gerbereichemie und Gerbereitechnologie
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£141.54
de Gruyter Phenole und Basen
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£134.09
De Gruyter Structural Principles of Unsaturated Organic
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£111.62
De Gruyter Einführung in die Chemie der Alkaloide
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£134.09
de Gruyter Fortschritte Der Alkaloidchemie Seit 1953
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£134.09
de Gruyter Laboratoriumstechnik Der Organischen Chemie
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£141.54
de Gruyter Organische Synthesen Mit Cyansäureestern
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£134.09
de Gruyter Allgemeine Organische Chemie
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£141.54
de Gruyter Polarographie Und Chemische Konstitution
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£134.09
de Gruyter Polyelektrolyte
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£134.09
de Gruyter Spezielle Untersuchungen Auf Dem Gebiet Der
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£134.09
Thieme Applications of Domino Transformations in Organic
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£282.23
Thieme Publishing Group Cross-Coupling Reactions, Workbench Edition
Book Synopsis In Science of Synthesis: Cross Coupling and Heck-Type Reactions, expert authors present and discuss the best and most reliable methods currently available for the formation of new carbon-carbon and carbon-heteroatom bonds using these reactions, highlighted with representative experimental procedures. Together, the three volumes of Cross Coupling and Heck-Type Reactions provide an extensive overview of the current state of the art in this field of central importance in modern chemistry, and are an invaluable resource for the practicing synthetic organic chemist. The Cross Coupling and Heck-Type Reaction set consists of the following volumes: Cross Coupling and Heck-Type Reactions 1: C-C Cross Coupling Using Organometallic Partners Cross Coupling and Heck-Type Reactions 2: Carbon-Heteroatom Cross Coupling and C-C Cross Couplings of Acidic C-H Nucleophiles Cross Coupling and Heck-Type Reactions 3: Metal-Catalyzed Heck-Type Reactions and C-H Couplings via C-H Activation
£499.05
Thieme Publishing Group Applications of Domino Transformations in Organic
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£280.81
Thieme Science of Synthesis Catalytic Reduction in
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£284.04
Thieme Science of Synthesis Catalytic Reduction in
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£284.04
Thieme Publishing Group Science of Synthesis: Knowledge Updates 2019/2
Book SynopsisThe Science of Synthesis Editorial Board, together with the volume editors and authors, is constantly reviewing the whole field of synthetic organic chemistry as presented in Science of Synthesis and evaluating significant developments in synthetic methodology. Several annual volumes updating content across all categories ensure that you always have access to state-of-the-art synthetic methodology.Table of Contents12.4.5 Benzimidazoles (Update 2019) 30.1.1.3 Acyclic O,N-Acetals (Update 2019) 30.1.2.3 Cyclic O,N-Acetals (Update 2019) 30.3.7.11 Deprotection of S,S-Acetals (Update 2019) 32.4.4 Chloro-, Bromo-, and Iodoalkenes (Update 2019) 33.1.13.3 2,3-Dihydrothiophenes and Derivatives (Update 2019) 33.1.14.3 3,4-Dihydro-2H-thiopyrans and Derivatives (Update 2019) 37.4.1.7 Synthesis of Five-Membered and Larger-Ring Oxacycloalk-3-enes by Ring-Closure Reactions, Except Ring-Closing Metathesis (Update 2019) 38.10 Metal-Catalyzed Syntheses of Peroxides
£3,011.56
Thieme Publishing Group Science of Synthesis: Knowledge Updates 2019/3
Book SynopsisThe Science of Synthesis Editorial Board, together with the volume editors and authors, is constantly reviewing the whole field of synthetic organic chemistry as presented in Science of Synthesis and evaluating significant developments in synthetic methodology. Several annual volumes updating content across all categories ensure that you always have access to state-of-the-art synthetic methodology.Table of ContentsVolume 14: Six-Membered Hetarenes with One Chalcogen 14.4 Product Class 4: Benzopyranones and Benzopyranthiones 14.9 Product Class 9: Benzothiopyranones and Benzothiopyranthiones 14.11 Product Class 11: Selenopyranones and Benzoselenopyranones Volume 34: Fluorine 34.1 Product Class 1: Fluoroalkanes Volume 38: Peroxides 38.8 Product Class 8: Monocyclic Peroxides
£3,011.56
Thieme Publishing Group Science of Synthesis: Advances in Organoboron
Book SynopsisThe widespread use of organoboron compounds justifies the efforts devoted to their synthesis, as well as toward developing an understanding of their reactivity. The nature of the mono- or diboron species is of paramount importance in determining the reversible covalent binding properties of the boron atom with both nucleophiles and electrophiles. By wedding the rich chemical potential of organoboron compounds to the ubiquity of organic scaffolds, advanced borylation reactions have the potential to open unprecedented synthetic alternatives, and new knowledge in the field should encourage chemists to use organoboron compounds. In this volume, the main objective is to provide a collection of the most useful, practical, and reliable methods, reported mainly within the last decade, for boron activation and boron reactivity. The volume covers the main concepts of organoboron compounds and includes experimental procedures, enabling newcomers to the field the instant and reliable application of the new tools in synthesis. Rather than aiming for a comprehensive coverage, the most advanced solutions for challenging transformations are introduced. To this end, a team of pioneers and leaders in the field have been assembled who discuss both the practical and conceptual aspects of this rapidly growing field.Table of Contents1 Introduction 2 Mechanistic Aspects of Carbon—Boron Bond Formation 3 Diboron Compounds: Synthesis and Applications 4 Synthesis of gem-Diboron Compounds from Diboron Reagents 5 anti Boron Addition to Alkynes 6 Borylation of Carbonyl and Imine Groups 7 Borylative Ring Opening 8 Borylative Ring Closing 9 Decarbonylative/Decarboxylative Borylation 10 Borylation Reactions in Water 11 Nanocatalyzed Borylation Reactions 12 Reactions through Radical Boryl Moieties 13 Boron "Ate" Complexes for Asymmetric Synthesis 14 Application of Selective Asymmetric Borylation to Target Compounds
£3,011.56
Thieme Publishing Group Spectroscopic Methods in Organic Chemistry
Book SynopsisBoost your knowledge of modern spectroscopic methods! This reference work provides you with essential knowledge for the application of modern spectroscopic methods in organic chemistry. All methods are explained based on typical practical examples, theoretical aspects, and applications. The following spectroscopic methods are explained and examples are given: UV/Vis Spectroscopy Infrared (IR) and Raman Spectroscopy Nuclear Magnetic Resonance Spectroscopy (NMR) Mass Spectrometry (MS) The textbook has been a standard reference for decades. As it conveys necessary knowledge for examinations at all universities it is compulsory reading for every organic chemistry student!Table of Contents1 UV/Vis Spectroscopy 1.1 Theoretical Introduction 1.2 Sample Preparation and Measurement of Spectra 1.3 Chromophores 1.4 Applications of UV/Vis Spectroscopy 1.5 Derivative Spectroscopy 1.6 Chiroptical Methods 2 Infrared and Raman Spectra 2.1 Introduction 2.2 Basic Principles 2.3 Infrared Spectrometer 2.4 Sample Preparation 2.5 Infrared Spectrum 2.6 Characteristic Absorptions: An Overview 2.7 Infrared Absorptions of Single Bonds with Hydrogen 2.8 Infrared Absorptions of Triple Bonds and Cumulated Double Bonds 2.9 Infrared Absorptions of Double Bonds C=O, C=N, N=N, and N=O 2.10 Infrared Absorption of Aromatic Compounds 2.11 Infrared Absorption in the Fingerprint Range 2.12 Examples of Infrared Spectra 2.13 Information Technology Assisted Spectroscopy 2.14 Quantitative Infrared Spectroscopy 2.15 Raman Spectroscopy 3 Nuclear Magnetic Resonance Spectroscopy 3.1 Physical Principles 3.2 NMR Spectra and Molecular Structure 3.3 1H NMR Spectroscopy 3.4 13C NMR Spectroscopy 3.5 Combination of 1H and 13C NMR Spectroscopy 3.6 NMR of other Nuclei 4 Mass Spectrometry 4.1 Introduction 4.2 General Aspects of Mass Spectrometry 4.3 Instrumental Aspects 4.4 Interpretation of Spectra and Structural Elucidation 4.5 Sample Preparation 4.6 Artifacts 4.7 Tables to the Mass Spectrometry 5 Handling of Spectra and Analytical Data: Practical Examples 5.1 Introduction 5.2 Characterization of Compounds 5.3 Structure Elucidation of Allegedly Known Compounds and of Products Arising from Syntheses 5.4 Structure Elucidation of COmpletely Unknown Compounds
£69.30
Thieme Publishing Group Science of Synthesis: Knowledge Updates 2023/1
Book SynopsisThe Science of Synthesis Editorial Board, together with the volume editors and authors, is constantly reviewing the whole field of synthetic organic chemistry as presented in Science of Synthesis and evaluating significant developments in synthetic methodology. Several annual volumes updating content across all categories ensure that you always have access to state-of-the-art synthetic methodology.Table of Contents47.1.1.4.12 Synthesis of Alkenes by Palladium-Catalyzed Cross-Coupling Reactions with Carbene Precursors 47.1.2.1.5 Synthesis of Alkenes by Cross-Coupling and Heck Reactions 47.1.2.1.6 Alkyl-Mizoroki–Heck-Type Reactions 47.1.2.3.3 Asymmetric π-Allyl Substitution Reactions 47.1.2.5 Allylic C—H Functionalization 47.1.4.11 Synthesis of Alkenes by α,β-Dehydrogenation 47.1.5.2.3 Synthesis of Alkenes via Hydrogenation of Alkynes and Allenes 47.1.5.5 Synthesis of Alkenes via Metal-Catalyzed Hydrofunctionalizations 47.1.5.6 Synthesis of Functionalized Alkenes by Metal-Catalyzed Coupling of Carbonyls with Alkynes/Allenes 47.1.5.7 Synthesis of Alkenes via Radical Addition Reactions
£3,011.56
Springer International Publishing AG Brewing Science: A Multidisciplinary Approach
Book SynopsisThis text finally collects all the introductory aspects of beer brewing science into one place for undergraduate brewing science courses. This expansive and detailed work is written in conversational style, walking students through all the brewing basics from the origin and history of beer to the brewing process to post-brew packaging and quality control and assurance. As an introductory text, this book assumes the reader has no prior knowledge of brewing science and only limited experience with chemistry, biology and physics. The text provides students with all the necessary details of brewing science using a multidisciplinary approach, with a thorough and well-defined program of in-chapter and end-of-chapter problems. As students solve these problems, they will learn how scientists think about beer and brewing and develop a critical thinking approach to addressing concerns in brewing science. As a truly comprehensive introduction to brewing science, Brewing Science: A Multidisciplinary Approach walks students through the entire spectrum of the brewing process. The different styles of beer, the molecular makeup and physical parameters, and how those are modified to provide different flavors are listed. All aspects of the brewery process, from the different setup styles to sterility to the presentation of the final product, are outlined in full. All the important brewing steps and techniques are covered in meticulous detail, including malting, mashing, boiling, fermenting and conditioning. Bringing the brewing process full circle, this text covers packaging aspects for the final product as well, focusing on everything from packaging technology to quality control. Students are also pointed to the future, with coverage of emerging flavor profiles, styles and brewing methods. Each chapter in this textbook includes a sample of related laboratory exercises designed to develop a student’s capability to critically think about brewing science. These exercises assume that the student has limited or no previous experience in the laboratory. The tasks outlined explore key topics in each chapter based on typical analyses that may be performed in the brewery. Such exposure to the laboratory portion of a course of study will significantly aid those students interested in a career in brewing science.Table of ContentsIntroduction to Brewing Science.- Beer Styles.- Molecules and Other Matters.- Overview of the Brewing Process.- The Food for the Brew.- Mashing.- Sparging.- Wort Boiling.- Cooling and Fermenting.- Conditioning.- Packaging.- Quality Assurance and Quality Control.- Appendix A.- Appendix B.
£54.99
Springer International Publishing AG Biotransformations in Organic Chemistry: A
Book SynopsisThis well-established textbook on biocatalysis provides a basis for undergraduate and graduate courses in modern organic chemistry, as well as a condensed introduction into this field. After a basic introduction into the use of biocatalysts—principles of stereoselective transformations, enzyme properties and kinetics—the different types of reactions are explained according to the 'reaction principle', such as hydrolysis, reduction, oxidation, C–C bond formation, etc. Special techniques, such as the use of enzymes in organic solvents, immobilization techniques, artificial enzymes and the design of cascade-reactions are treated in a separate section. A final chapter deals with the basic rules for the safe and practical handling of biocatalysts.The use of biocatalysts, employed either as isolated enzymes or whole microbial cells, offers a remarkable arsenal of highly selective transformations for state-of-the-art synthetic organic chemistry. Over the last two decades, this methodology has become an indispensable tool for asymmetric synthesis, not only at the academic level, but also on an industrial scale. In this 7th edition new topics have been introduced which include alcohol and amine oxidases, amine dehydrogenases, imine reductases, haloalkane dehalogenases, ATP-independent phosphorylation, Michael-additions and cascade reactions. This new edition also emphasizes the use of enzymes in industrial biotransformations with practical examples.Table of Contents1 Introduction and Background Information1.1 Introduction..........................................................................................1.2 Common Prejudices Against Enzymes...............................................1.3 Advantages and Disadvantages of Biocatalysts..................................1.3.1 Advantages of Biocatalysts........................................................1.3.2 Disadvantages of Biocatalysts...................................................1.3.3 Isolated Enzymes vs. Whole Cell Systems.........................1.4 Enzyme Properties and Nomenclature...............................................1.4.1 Structural Biology in a Nutshell..............................1.4.2 Mechanistic Aspects of Enzyme Catalysis...........................1.4.3 Classification and Nomenclature............................................1.4.4 Coenzymes.......................................................................1.4.5 Enzyme Sources..............................................................References..... ................................................................................... 2 Biocatalytic Applications 2.1 Hydrolytic Reactions..........................................................................2.1.1 Mechanistic and Kinetic Aspects.............................................2.1.2 Hydrolysis of the Amide Bond................................................2.1.3 Ester Hydrolysis.......................................................................2.1.3.1 Esterases and Proteases.............................................2.1.3.2 Lipases.......................................................................2.1.3.3 Hydrolysis of Lactones.......................................................................2.1.4 Hydrolysis and Formation of Phosphate Esters......................2.1.5 Hydrolysis of Epoxides...........................................................2.1.6 Hydrolysis of Nitriles..............................................................2.2 Reduction Reactions..........................................................................2.2.1 Recycling of Cofactors............................................................2.2.2 Reduction of Aldehydes and Ketones Using Isolated Enzymes.....................................................2.2.3 Reduction of Aldehydes and Ketones Using Whole Cells....2.2.4 Reduction of C=N Bonds .......................2.2.5 Reduction of C=C-Bonds .......................2.3 Oxidation Reactions..........................................................................2.3.1 Oxidation of Alcohols and Aldehydes...................................2.3.2 Oxidation of Amines ...................................2.3.3 Oxygenation Reactions...........................................................2.3.3.1 Hydroxylation of Alkanes........................................2.3.3.2 Hydroxylation of Aromatic Compounds.................2.3.3.3 Epoxidation of Alkenes............................................2.3.3.4 Sulfoxidation Reactions............................................2.3.3.5 Baeyer-Villiger Reactions.........................................2.3.3.6 Formation of Hydroperoxides.............................................2.3.3.7 Dihydroxylation of Aromatic Compounds and Conjugated C=C Bonds...............2.3.4 Peroxidation Reactions............................................................2.4 Formation of Carbon-Carbon Bonds.................................................2.4.1 Aldol Reactions.......................................................................2.4.2 Thiamine-Dependent Acyloin and Benzoin Reactions.........2.5 Addition and Elimination Reactions.................................................2.5.1 Addition of Water........................................................2.5.2 Addition of Ammonia..........................................................2.5.3 Cyanohydrin Formation and Henry Reaction...........................................2.5.4 Michael-Type Additions............................................2.6 Transfer Reactions.............................................................2.6.1 Glycosyl Transfer Reactions..............................................2.6.1.1 Glycosyl Transferases........................................2.6.1.2 Glycoside phosphorylases and Trans-glycosidases........................................2.6.1.3 Glycosidases........................................2.6.2 Amino Transfer Reactions...................................................2.7 Halogenation and Dehalogenation Reactions...................................2.7.1 Halogenation...........................................................................2.7.2 Dehalogenation.......................................................................References....................................................................................... 3 Special Techniques 3.1 Enzymes in Organic Solvents..........................................................3.1.1 Ester Synthesis........................................................................3.1.2 Lactone Synthesis...................................................................3.1.3 Amide Synthesis.....................................................................3.1.4 Peptide Synthesis....................................................................3.1.5 Peracid Synthesis....................................................................3.1.6 Redox Reactions.....................................................................3.1.7 Medium Engineering...............................................................3.2 Cascade Reactions...............................................................3.3 Immobilization..................................................................................3.4 Artificial and Modified Enzymes.....................................................3.4.1 Artificial Enzyme Mimics.....................................................3.4.2 Modified Enzymes.......................................................... 3.4.2.1 Chemically Modified Enzymes................................3.4.2.2 Genetically Modified Enzymes................................3.4.3 Catalytic Antibodies................................................................References........................................................................................ 4 State of the Art and Outlook................................................................. 5 Appendix 5.1 Basic Rules for Handling Biocatalysts..............................................5.2 Abbreviations....................................................................................5.3 Suppliers of Enzymes.......................................................................5.4 Commonly Used Enzyme Preparations...........................................5.5 Major Culture Collections................................................................5.6 Pathogenic Bacteria and Fungi........................................................
£67.49
Springer International Publishing AG Modern Ylide Chemistry: Applications in Ligand
Book SynopsisThis volume covers recent advances in the chemistry of ylidic compounds with focus on their application in the design of ligands with unique donor properties, the development of novel organic transformations as well as the use of ylides in homogenous catalysis. Thereby, this volume particularly aims at the community of organic and organometallic chemists engaged in synthetic chemistry and catalysis as well as in the use of special ligands for the stabilization of unusual main group element species and the “transition-metal free” activation of element-element/hydrogen bonds. These fields of research are highly active and vivid research areas to which ylide chemistry has only recently started to contribute, but has already led to fascinating developments in most different directions. This volume highlights these recent developments, thus giving not only an overview over the past achievements, but also possibilities for future applications. To this end, the chapters selected in this volume combine different aspects of ylide chemistry, starting with theoretical aspects in ligand design followed by synthetic organic methods, catalytic transformations and complex chemistry. Table of ContentsStructure and Reactivity of Carbones and Ylide Stabilized Carbenes: Contributions from Theory.- Synthesis, Structure, and Reactivity of Carbodiphosphoranes,Carbodicarbenes,and Related Species.- Synthesis and Structure of Carbodicarbenes and Their Application in Catalysis.- Sulfur Ylides in Organic Synthesis and Transition Metal Catalysis.- Reactivity and Applications of α-Metalated Ylides.
£187.49
Springer Fachmedien Wiesbaden Biochemie: Grundlagen und Experimente
Book SynopsisGrundwissen in Biochemie und die Durchführung von Versuchen mit Biomolekülen setzen die Kenntnis chemischer Zusammenhänge, Reaktionsweisen und Stoffeigenschaften voraus. Im Zentrum dieses Buches stehen grundsätzliche Stoffeigenschaften, Enzyme, zentrale Stoffwechselreaktionen und Metabolite. Nach einer kurz gefassten Einführung in das jeweilige Kapitelthema werden umfangreiche Versuche beschrieben, die am Ende in Form von weiterführenden Fragestellungen zusammengefasst und vertieft werden. Ziel des Buches ist es, Studierenden aller Naturwissenschaften Biochemie im Grundstudium zu vermitteln. Durch seine umfassende Anlage kann es aber auch im Hauptstudium und im Laboralltag als Nachschlagewerk herangezogen werden.Table of ContentsArbeiten im biochemischen Labor - Chemische und physikalische Grundlagen - Aminosäuren und Proteine - Enzymkatalyse, Enzyme und Coenzyme - Zucker und Polysaccharide - Phosphat und Nucleotide - Nucleinsäuren - Zellorganellen - Biochemische Trenn- und Analysenverfahren - Tabellen - Nomogramme
£31.34
Springer Fachmedien Wiesbaden Biomaterialien und Biomineralisation: Eine
Book SynopsisBiomaterialien ersetzen verloren gegangene Körperfunktionen, entweder allein oder in Kombination mit elektrischen oder elektronischen Bauteilen. Künstliche Haut, künstliche Adern, künstlicher Knochen, Hüftprothesen, Herzschrittmacher, Implantate, Zahnersatz: Alle diese Errungenschaften der modernen Medizin beruhen letztlich auf geeigneten Werkstoffen, die sowohl biologischen als auch chemischen und mechanischen Ansprüchen genügen müssen. Zur Entwicklung bedarf es der gemeinsamen Kompetenz von Medizinern, Chemikern, Physikern, Biologen und Ingenieuren. Das Buch soll in die notwendigen Grundlagen in einer für alle diese Ausbildungsrichtungen verständlichen Weise einführen.Trade Review"Nicht umsonst wendet sich diese Einführung nicht nur an Chemiker, sondern allgemein an Naturwissenschaftler, Mediziner und Ingenieure. Dem Leser - insbesondere dem älteren - wird beim Lesen dieses Buches deutlich, wie weit die Medizin auf andere Wissenschaften wie die Chemie angewiesen ist und wie der medizinische Fortschritt auf den Erkenntnissen der Chemie beruht. Deswegen ist das Buch lesenswert insbesondere für denjenigen, der "etwas mehr" wissen möchte als sein Arzt..." www.chemieonline.de, 06.08.2007 "Es ist dem Autor in hervorragender Weise gelungen, jeweils eine kompakte, präzise und anschauliche Einführung der Grundbegriffe zu geben um sie dann sofort für die Formulierung fundamentaler Aussagen zu verwenden, die nicht nur für Chemiker, Biologen und Mediziner unentbehrlich sind, sondern auch zum geistigen Haushalt eines jeden allgemein gebildeten Menschen gehören sollten. [...] Dieses Buch ist ein Musterbeispiel dafür, wie Naturwissenschaft im Kontext vermittelt werden kann. Praxis der Naturwissenschaften, 08/2004Table of ContentsChemie fester Stoffe - Festkörpermechanik und Biomechanik - Stoffklassen von Biomaterialien - Herstellungsverfahren für Biomaterialien - Chemische Testverfahren - Mechanische Testverfahren - Biologische Testverfahren - Beispiele für Biomaterialien - Wichtige Biomaterialien - Bildung von Biomineralien - Biomaterialentwicklung
£23.74
Springer Fachmedien Wiesbaden Kurze Einführung in die Chemie der Heterocyclen
Book SynopsisDiese einführende Darstellung beschränkt sich auf die Darstellung der wesentlichen heterocyclischen Grundtypen und deren Eigenschaften und Synthesen. Ausgewählte Beispiele aus der aktuellen Literatur sollen das Interesse am selbständigen weiteren Studium wecken.Table of Contents1 Einleitung.- 1.1 Nomenklatur.- 1.2 Unterteilung der Heterocyclen.- 1.2.1 Heterocycloalkane.- 1.2.2 Heterocycloalkene.- 1.2.3 Heteroaromaten.- 2 Drei-und Vierringheterocyclen.- 2.1 Epoxide (Oxirane).- 2.1.2 Herstellung.- 2.1.2 Reaktionen.- 2.2 Thiirane (Episulfide).- 2.2.1 Herstellung.- 2.2.2 Reaktionen.- 2.3 Aziridine (Ethylenimine).- 2.4 Oxaziridine.- 2.4.1 Herstellung.- 2.4.2 Reaktionen.- 2.5 Diazirine, Diaziridine.- 2.5.1 Herstellung und Reaktionen.- 2.6 Oxetidine (?-Lactone).- 2.7 Azetidin.- 3.0 Fünfring-Heterocyclen mit einem Heteroatom.- 3.1 Furan.- 3.1.1 Herstellung.- 3.1.2 Reaktionen.- 3.2 Thiophen.- 3.2.1 Herstellung.- 3.2.2 Reaktionen.- 3.3 Pyrrol.- 3.3.1 Herstellung.- 3.3.2 Reaktionen.- 3.3.3 Naturstoffderivate des Pyrrols.- 4 Benzokondensierte Fünfring-Heterocyclen.- 4.1 Cumaron.- 4.2 Indol.- 4.2.1 Herstellung.- 4.2.2 Reaktionen.- 4.2.3 Indolalkaloide.- 5 Sechsring-Heterocyclen mit einem Heteroatom (Pyrane, Pyrone).- 5.1 Pyrane.- 5.2 Pyrone.- 5.3 Pyridin.- 5.3.1 Herstellung.- 5.3.2 Reaktionen.- 5.3.3 Derivate.- 5.3.4 Derivate mit biochemischer und biologischer Bedeutung.- 5.4 Synthese des Pyridoxals.- 6 Benzokondensierte Sechsring-Heterocyclen.- 6.1 Benzopyrane.- 6.1.1 Herstellung.- 6.1.2. Naturstoffderivate der Chromane und Chromone.- 6.2 Benzopyridine.- 6.2.1 Herstellung.- 6.3 Isochinolin.- 6.3.1 Herstellung.- 6.4 Naturstoffderivate des Chinolins.- 7 Fünfringheterocyclen mit mehreren Heteroatomen.- 7.1 Oxazol.- 7.1.1 Herstellung.- 7.1.2 Reaktionen.- 7.2 Isoxazol.- 7.2.1 Herstellung.- 7.3 Thiazol.- 7.3.1 Herstellung.- 7.3.2 Thiazolderivate mit biologischer Bedeutung.- 8 Fünfringheterocyclen mit mehreren N-Atomen.- 8.1 Pyrazol.- 8.1.1 Herstellung.- 8.1.2 Reaktionen.- 8.2 Imidazol.- 8.2.1 Herstellung.- 8.2.2 Reaktionen.- 8.2.3 Wichtige Imidazolderivate.- 8.3 1,2,3-Triazol.- 8.3.1 Herstellung.- 8.3.2 Derivate.- 9 Sechsringheterocyclen mit mehreren N-Atomen.- 9.1 Dioxan.- 9.2 Dibenzodioxine.- 9.3 Morpholin.- 10 Sechsringheterocyclen mit mehreren N-Atomen.- 10.1 Pyridazin.- 10.2 Pyrimidin.- 10.2.1 Naturstoffderivate des Pyrimidins.- 10.3 Naturstoffderivate des Purins.- 10.4 Pterine.- 11 Siebenringheterocyclen.- Sachwörterverzeichnis.
£38.69
Springer Fachmedien Wiesbaden Übungen zur organischen Synthese
Book SynopsisDurch eine Vielzahl an Aufgaben und Beispielen vertieft dieses Übungsbuch Kenntnisse und Fähigkeiten auf dem Gebiet der präparativen Organischen Chemie. Jede der Aufgaben enthält ein Reaktionsschema, in dem sowohl Strukturen als auch Reagenzien ausgelassen sind und ergänzt werden müssen. Die Aufgaben sind als Herausforderung für Chemiestudenten und Chemiker auf verschiedenen Ausbildungsniveaus konzipiert. Der Leser soll aktiv an den vorgestellten Synthesen arbeiten und Lösungen vorschlagen, um dadurch sein Vokabular der organischen Synthesechemie zu erweitern.Table of Contents1. Totalsynthese von (?)-Ovatolid.- 2. Totalsynthese von RS-15385.- 3. Totalsynthese von Islandsäure-I-methylester.- 4. Synthese von (+)-Patulolid C.- 5. Asymmetrische Synthese von 1-Deoxy-8,8a-di-epi-castanospermin.- 6. Synthese von Hydantocidin-verwandten Strukturen.- 7. Totalsynthese von (±)-Leuhistin.- 8. Synthese von Cryptophycin C.- 9. Totalsynthese von (?)-Balanol.- 10. Asymmetrische Synthese eines Bryostatinfragments.- 11. Studien zur Synthese von Pseudopterosin.- 12. Totalsynthese von Neodolabellenol.- 13. Synthese von (?)-Swainsonin.- 14. Totalsynthese von Octalactin A und B.- 15. Asymmetrische Synthese der Milbemycin ?3 Spiroketaluntereinheit.- 16. Stereoselektive Synthese von (+)-Artemisinin.- 17. Synthese von (±)-Prosopinin.- 18. Synthese eines geschützten fluorierten carbocyclischen Nucleosids.- 19. Synthese von (±)-Oxerin.- 20. Synthese eines enantiomerenreinen C-4 funktionalisierten 2-Iodcyclohexanonacetals.- 21. Synthese des Tropanalkaloids Calystegin A3.- 22. Totalsynthese von (?)-Solavetivon.- 23. Totalsynthese von (+)-Himbacin.- 24. Synthese von 5-Hydroxytiagabin.- 25. Studien zur Synthese von Zoanthaminalkaloiden.- 26. Totalsynthese von 1233A.- 27. Synthese eines Schlüsselintermediats von 1ß;-Methylcarbapenen Antibiotika.- 28. Totalsynthese eines Fragments von Hennoxazol A.- 29. Totalsynthese von (+)-Duocarmycin A.- 30. Studien zur Totalsynthese von Rapamycin.- 31. Studien zur Totalsynthese von Rapamycin.- 32. Studien zur Totalsynthese von Rapamycin.- 33. Synthese von Isochromanchinonen.- 34. Synthese eines D-chiro-Inosit-1-phosphats.- 35. Stereoselektive Synthese von (±)-Aromaticin.- 36. Synthese von 7-Methoxycyclopropamitosen.- 37. Totalsynthese von (+)-?-Lycoran.- 38. Synthese von (±)-12a-Desoxytetracyclin.- 39. Enantioselektive Totalsynthese von (?)-7-Deacetoxyalcyoninacetat.- 40. Totalsynthese von (+)-Tetrahydrocerulenin.- 41. Totalsynthese von (+)-Longifolen.- 42. Studien zur Totalsynthese von Cerorubensäure-III.- 43. Totalsynthese von 10-Decarboxychinocarcin.- 44. Totalsynthese von (+)-Pyripyropen A.- 45. Totalsynthese von d,l-Isospongiadiol.- 46. Totalsynthese des Stemonaalkaloids (?)-Stenin.- 47. Totalsynthese von (?)-Papuamin.- 48. Totalsynthese von (+)-Stoechospermol.- 49. Synthese der C8–C19 Untereinheit von Rapamycin.- 50. Synthese des AB-Rings von Ciguatoxin.- 51. Totalsynthese von (+)-Carbonolid B.- 52. Studien zum Kohlenstoffgerüst von Asteriscanolid.- 53. Totasynthese von (+)-DoIabellatrienon.- 54. Synthese von 3?-Acetoxydrimenin.- 55. Totalsynthese von (+)-Adrenosteron.- 56. Totalsynthese von Stenin.- 57. Totalsynthese von (?)-Suaveolin.- 58. Enantioselektive Synthese von Deoxynojirimycin.- 59. Synthese von (±)-Aphidicolin.- 60. Totalsynthese von (+)-7-Deoxypancratistatin.- 61. Synthetische Studien zu Bruceantin.- 62. Totalsynthese von (+)-FR900482.- 63. Totalsynthese von (3Z)-Dactomelyn.- 64. Totalsynthese von (±)-Acerosolid.- 65. Synthese einer Vindorosinvorstufe.- 66. Synthese von (?)-PGE2-Methylester.- 67. Totalsynthese von (?)-Parviflorin.- 68. Totalsynthese von (?)-Chlorthricolid.- 69. Synthetische Studien zu Furanoheliangoliden.- 70. Totalsynthese von Staurosporin.- 71. Totalsynthese von (?)-Cephalotaxin.- 72. Synthese von Picrotoxinin.- 73. Totalsynthese von (+)-Dactylol.- 74. Synthese von (±)-Ceratopicanol.- 75. Totalsynthese von (±)-Myrocin C.- 76. Synthese von Staurosporin-Aglycon.- 77. Synthese von (20S)-Camptothecin.- 78. Synthese eines Fragments von (+)-Codaphniphyllin.- 79. Totalsynthese von Indanomycin.- 80. Totalsynthese von Taxol.- 81. Totalsynthese von (?)-Grayanotoxin III.- 82. Enantioselektive Totalsynthese von (?)-Strychnin.
£31.34
Wiley-VCH Verlag GmbH Classics in Total Synthesis: Targets, Strategies,
Book SynopsisK.C. Nicolaou - Winner of the Nemitsas Prize 2014 in Chemistry This book is a must for every synthetic chemist. With didactic skill and clarity, K. C. Nicolaou and E. Sorensen present the most remarkable and ingenious total syntheses from outstanding synthetic organic chemists.To make the complex strategies more accessible, especially to the novice, each total synthesis is analyzed retrosynthetically. The authors then carefully explain each synthetic step and give hints on alternative methods and potential pitfalls. Numerous references to useful reviews and the original literature make this book an indispensable source of further information.Special emphasis is placed on the skillful use of graphics and schemes: Retrosynthetic analyses, reaction sequences, and stereochemically crucial steps are presented in boxed sections within the text. For easy reference, key intermediates are also shown in the margins.Graduate students and researchers alike will find this book a gold mine of useful information essential for their daily work. Every synthetic organic chemist will want to have a copy on his or her desk.Table of ContentsConstructing the Molecules of Nature Strychnine (Woodward) Strychnine (Overman) Penicillin V (Sheehan) Reserpine (Woodward) Vitamin B12 (Woodward) Progesterone (Johnson) Prostaglandins F2-alpha and E2 (Corey) Prostaglandins A2 and F2-alpha (Stork) Carpanone (Chapman) Monensin (Kishi) Monensin (Still) Biotin (Baggiolini) Periplanone B (Still) Periplanone B (Schreiber) Isocomene (Pirrung) Estrone (Vollhardt) Erythronolide B (Corey) Endiandric Acids A-G (Nicolaou) Thienamycin (Merck) Asteltoxin (Schreiber) Amphotericin B (Nicolaou) L-Hexoses (Masamune & Sharpless) Cytovaricin (Evans) Indolizamycin (Danishefsky) Ginkgolide B (Corey) Paoniflorigenin and Paoniflorin (Corey) Methyl homosecodaphniphyllate (Heathcock) Gilvocarcin M and V (Suzuki) Calicheamicin gamma-1I (Nicolaou) Taxol (Nicolaou) Rapamycin (Nicolaou) Menthol (Noyori) Palytoxin (Kishi) Brevetoxin B (Nicolaou)
£77.40
Wiley-VCH Verlag GmbH Organic Synthesis Workbook
Book SynopsisFrom the Foreword written by Erick M. Carreira: "... The Organic Synthesis Workbook is an ideal compilation of state-of-the art modern syntheses which wonderfully showcases the latest advances in synthetic chemistry in combination with fundamentals in a question-and-answer format. The structure of the book is such that the reader can appreciate the intricacies of strategic planning, reagent tailoring, and structural analysis within the context of the individual synthetic targets. In providing highlights of synthesis from a wider range of natural products classes (alkaloids, terpenes, macrolides) the reader is given a tour through a broad range of reaction chemistry and concepts. Moreover, because in its scope the authors have ignored international borders, the book effectively parlays the global aspect of current research in the exciting field of organic synthesis... The Organic Synthesis Workbook promises to be to the current generation of graduate students, and even "students-for-life", what Ireland's and Alonso's books were to those of us who were graduate students in the 80's [Alsono: The Art of Problem Solving in Organic Chemistry, Ireland: Organic Synthesis]. The authors have wonderfully captured the thrill, the enjoyment, and the intellectual rigor that is so characteristic of modern synthetic organic chemistry."Trade Review"...succeeds admirably in explaining in context many important principles of contemporary organic synthesis. This book is reasonably priced and I recommend Organic Synthesis Workbook to you highly." Applied OrganometallicchemistyTable of ContentsVeticadinol Mamanuthachinon (-)Swanisonin (-)Capnellen (-)Epothilon Erythronolid A Tautomycin Thujon (+)Camptothecin (+)Streptazolin Amyrin (+)Asimycin (Z)Dactomelyn Maehrs Roflamycoin Fluvirucin - Aglycon
£54.86
Wiley-VCH Verlag GmbH Esterification: Methods, Reactions, and
Book SynopsisGathering together the widespread literature in the field, this monograph acts as a reference guide to this very important chemical reaction. Following an introduction, the book goes on to discuss methodology, before treating synthetic and industrial applications -- the latter being a new focus in this completely revised, updated and extended second edition. A must-have for organic, natural products and catalytic chemists, as well as those working in industry, of for lecturers in chemistry.Trade Review"...Otera's book does a good job, concisely covering the esterification methodology literature from 1990 to 1999, and that survey will be useful to synthetic organic chemists..." Angewandte Chemie IE, Vol. 43"Insgesamt gesehen ist das Buch für Chemiker auf dem Gebiet der organischen Synthese sehr nützlich." Philip J. Kocienski, School of Chemistry, University of Leeds (Großbritannien) Angewandte Chemie 10/04Table of ContentsPreface Introduction PART 1: Methodology REACTION OF ALCOHOLS WITH CARBOXYLIC ACIDS AND THEIR DERIVATIVES Reaction with Carboxylic Acids Reaction with Esters: Transesterification Reaction with Acid Anhydrides Reaction with Acid Halides and Other Acyl Derivatives USE OF TIN AND OTHER METAL ALKOXIDES CONVERSION OF CARBOCYLIC ACIDS TO ESTERS WITHOUT USE OF ALCOHOLS Reaction with Diazomethane Reaction with Alkyl Halides Reaction with Other Electrophiles ESTER-INTERCHANGE REACTION PART 2: Synthetic Applications KINETIC RESOLUTION Enzymatic Resolution Nonenzymatic Resolution Dynamic Kinetic Resolution Parallel Kinetic Resolution ASYMMETRIC DESYMMETRIZATION MISCELLANEOUS TOPICS Selective Esterification Use of Theoretical Amounts of Reactants New Reaction Media New Technologies Applications to Natural Products Synthesis INDUSTRIAL USES Ethyl Acetate Acrylic Esters Polyesters Oils and Fats Biodiesel Fuel Amino Acid Esters Macrolides Flavoring Agents and Fragrances Pyrethroids
£158.35
Wiley-VCH Verlag GmbH Chemical Biology: Learning through Case Studies
Book SynopsisThis first book to adopt a problem-based approach teaches the true basics of the subject through illustrated everyday case studies. The editor's extensive experience in writing textbooks and his close relationship to the authors ensure that the contributions are presented in a pedagogically uniform and highly motivating fashion. Each chapter introduces a different biological problem taken from everyday lab work, such that students learn how to think in order to solve problems in biology by using techniques and tools taken from chemistry. A must-have for students in chemistry, biology and biochemistry.Trade Review"This first book to adopt a problem-based approach teaches the true basics of the subject through illustrated everyday case studies. Each chapter introduces a different biological problem taken from everyday lab work, such that students learn how to solve problems in biology by using techniques and tools taken from chemistry." METALL (1/2 2010)Table of ContentsYEAST-BASED CHEMICAL GENOMIC APPROACHES Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation - Chemogenomic Profiling: Elucidating the Mode of Action of Small Molecules MIRCOARRAY-BASED STRATEGIES TO IDENTIFY UNKNOWN PROTEIN INTERACTIONS Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation COMPOUND COLLECTION SYNTHESIS FOR CHEMICAL BIOLOGY Introduction Chemical Probes - A Chemical Question with Biological Consequences Diversity Oriented Synthesis (DOS) Biology Oriented Synthesis (BIOS) TARGET IDENTIFICATION AND VALIDATION OF A WNT/BETA-CATENIN PATHWAY MODULATOR Introduction Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation ACTIVITY-BASED PROTEIN PROFILING OF CYS PROTEASES Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation THE USE OF PHOTOAFFINITY LABELING FOR THE IDENTIFICATION OF THE BINDING SITE OF THE ANTIBIOTIC LINEZOLID Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation SURGICAL STRIKES: USES OF ANALOG SENSITIVE TECHNOLOGIES TO TARGET KINASES OF INTEREST Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation: ASKA Technology - Applications in Molecular Biology MODULATION OF PROTEIN-PROTEIN INTERACTIONS BY SMALL MOLECULES Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation TARGETED PROTEIN DEGRADATION IN LIVE CELLS Introduction The Biological Problem The Chemical Approach TRAPOXIN B: FROM TOTAL SYNTHESIS TO EPIGENETICS Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation NATIVE CHEMIAL LIGATION - A TOOL FOR CHEMICAL PROTEIN SYNTHESIS Introduction The Synthetic Challenge The Chemical Approach - Native Chemical Ligation Chemical Biological Research/Evaluation - The Ras-RBD Systems USING SPLIT INTEINS TO PREPARE SEMI-SYNTHETIC PROTEINS AND TO STUDY THE MECHANISMS OF PROTEIN TRANS-SPLICING Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation ELUCIDATION OF THE RAS CYCLE WITH SEMI-SYNTHETIC PROTEINS Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation THE STUDY OF RAB GTPASE RECYCLING USING SEMI-SYNTHETIC PRENYLATED PROTEINS Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation DEVELOPMENT OF A MODEL CANCER VACCINE CANDIDATE BASED ON THE MUCl CELLULAR SURFACE GLYCOPEPTIDE EPITOPE Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation THE INTRODUCTION OF CHEMICAL REPORTER GROUPS BY BIOORTHOGONAL LIGATION REACTIONS FOR THE IMAGING OF CELL-SURFACE GLYCANS Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation SEQUENCE SPECIFIC DNA-BINDING SMALL MOLECULES FOR PROTEIN RECRUITMENT AND MODULATION OF TRANSCRIPTION Introduction The Biological Problem - Targeting DNA with Small Molecules The Chemical Approach: The Polyamide Rationale Chemical Biological Research/Evaluation - Polyamides in Biological Applications G-QUADRUPLEX LIGANDS AS TOOLS FOR ELUCIDATING C-MYC TRANSCRIPTIONAL REGULATION Introduction The Biological Problem The Chemical Approach Chemical Biological Research/Evaluation
£46.71
Wiley-VCH Verlag GmbH Handbook of Synthetic Photochemistry
Book SynopsisUnique in its focus on preparative impact rather than mechanistic details, this handbook provides an overview of photochemical reactions classed according to the structural feature that is built in the photochemical step, so as to facilitate use by synthetic chemists unfamiliar with this topic. An introductory section covers practical questions on how to run a photochemical reaction, while all classes of the most important photocatalytic reactions are also included. Perfect for organic synthetic chemists in academia and industry.Trade Review"Given its organization and practical emphasis, I believe that this book would make an outstanding addition to the library of any synthetic organic chemist. It should certainly be on the acquisition lists of all institutional libraries." (Journal of the American Chemical Society, November 2010) Table of ContentsPHOTOCHEMICAL METHODS Photochemistry and Organic Synthesis Irradiation Apparatus Further Experimental Parameters Photochemical Steps in Synthesis CARBON-CARBON BOND FORMATION BY PHOTOELIMINATION OF SMALL MOLECULES IN SOLUTION AND IN CRYSTALS Introduction Photochemical C-C Bond Formation in Solution Reactions in the Solid State Conclusions INTERMOLECULAR ADDITION REACTIONS ONTO C-C MULTIPLE BONDS Introduction Addition to C-C Double Bonds Addition to C-C Triple Bonds Conclusions FORMATION OF A 3-MEMBERED RING Introduction Di-Pi-Methane Rearrangement Oxa-Di-Pi-Methane Rearrangement and Related Rearrangements [2+1] Cycloaddition of Alkenes with Carbenes Formation of a Cyclopropane Via Intramolecular Hydrogen Abstraction [3+2] Cycloaddition of Arenes with Alkenes Photochemical Synthesis of Three-Membered Heterocycles FORMATION OF A 4-MEMBERED RING I Introduction [2+2]-Photocycloaddition of Non Conjugated Alkenes [2+2]-Photocycloaddition of Aromatic Compounds Photochemical Electrocyclic Reactions Intramolecular Gamma-Hydrogen Abstraction (Yang Reaction) Metal Catalyzed Reactions Various Methods Conclusions FORMATION OF A 4-MEMBERED RING II Introduction [2+2]-Photocycloaddition of Enones (Substrate Type A1) [2+2]-Photocycloaddition of Vinylogous Amides and Esters (Substrate Clases A2 and A3) [2+2]-Photocycloaddition of Alpha, Beta-Unsaturated Carboxylic Acid Derivatives (Substrate Classes A4, A5 and A6) Conclusions and Perspectives FORMATION OF A 4-MEMBERED RING III (OXETANES) Introduction Generally Accepted Mechanisms of the Paterno-Buchi Reaction Regio- and Siteselective Synthesis of Oxetanes Stereoselective Syntheses of Oxetanes Conclusive Remarks FORMATION OF A 5-MEMBERED RING Formation of Five-Membered Ring: Intramolecular Delta-H Abstraction Formation of Five-Membered Rings Via [3+2]-Cycloadditions Photochemical Electrocyclization Reactions: Synthesis of Fused Five-Membered Ring Compounds Photoinduced Electron Transfer Radical Cation Mediated Cyclizations: Synthesis of Five-Membered Carbocyclic as well as Heterocyclic Ring Systems FORMATION OF 6-MEMBERED RING (AND LARGER RINGS) Introduction Photoelectron Transfer Initiated Cyclizations Photoinduced 6Pi-Electrocyclization Photocycloaddition Reactions Remote Intramolecular Hydrogen Abstraction Ring Contraction and Ring Enlargement Other Reactions Summary AROMATIC AND HETEROAROMATIC SUBSTITUTION BY SRN1 AND SN1 REACTIONS Introduction General Mechanistic Features Carbon-Carbon Bond Formation Carbon-Heteroatom Bond Formation Synthesis of Bi, Tri, and Poliaryls Synthesis of Carbocycles and Heterocycles SINGLET OXYGEN AS A REAGENT IN ORGANIC SYNTHESIS Introduction Dioxetanes Endoperoxides Allylic Hydroperoxides Tandem Singlet Oxygen Reactions Conclusion SYNTHESIS OF HETEROAROMATICS VIA REARRANGEMENT REACTIONS Introduction Synthesis of Five-Membered Rings with One Heteroatom Synthesis of Five-Membered Rings with Two Heteroatoms Synthesis of Five-Membered Rings with Three Heteroatoms Synthesis of Six-Membered Rings Synthesis of Seven-Membered Rings Concluding Remarks PHOTOLABILE PROTECTING GROUPS IN ORGANIC SYNTHESIS Introduction Photolabile Protecting Groups Chromatic Orthogonality Two-Photons Absorption Perspectives and Conclusion
£128.66
Wiley-VCH Verlag GmbH The Chemistry of Heterocycles: Structures,
Book SynopsisThis classical textbook in the best sense of the word is now completely revised, updated and with more than 40% new content. The approved ordering system according to the ring size of the heterocycles has been retained, while the important chapter on 'Problems and their Solutions' has been almost completely renewed by introduction of up-to-date scientific exercises, resulting in a great tool for self-testing and exams. There was maintained a chapter on nomenclature and a helpful index of name reactions. With approximately 1,000 new literature citations, this book remains a brilliant gateway to modern heterocyclic science for master and graduate students, as well as PhDs and researchers entering the field. 'If you want quick information about the basic (or acidic!) properties of a heterocycle, some interesting facts, or an assorted few ways of making it, this book provides a welcoming, accurate, and concise introduction.' Angewandte Chemie IE 'Eicher and Hauptmann provide an up to date introduction to the field for the advanced undergraduate and graduate students. ... The book is carefully produced to a very high standard.' European Journal of Medicinal ChemistryTable of ContentsPreface to the Third Edition IX Abbreviations and Symbols XI 1 The Structure of Heterocyclic Compounds 1 Reference 4 2 Systematic Nomenclature of Heterocyclic Compounds 5 2.1 Hantzsch-Widman Nomenclature 6 2.2 Replacement Nomenclature 11 2.3 Examples of Systematic Nomenclature 12 2.4 Important Heterocyclic Systems 15 3 Three-Membered Heterocycles 17 3.1 Oxirane 17 3.2 Thiirane 26 3.3 2H-Azirine 29 3.4 Aziridine 32 3.5 Dioxirane 37 3.6 Oxaziridine 38 3.7 3H-Diazirine 40 3.8 Diaziridine 40 References 41 4 Four-Membered Heterocyles 45 4.1 Oxetane 45 4.2 Thietane 49 4.3 Azete 50 4.4 Azetidine 51 4.5 1,2-Dioxetane 55 4.6 1,2-Dithiete 57 4.7 1,2-Dihydro-1,2-diazete 58 4.8 1,2-Diazetidine 58 References 59 5 Five-Membered Heterocycles 61 5.1 Furan 61 5.2 Benzo[b]furan 80 5.3 Isobenzofuran 84 5.4 Dibenzofuran 86 5.5 Tetrahydrofuran 87 5.6 Thiophene 90 5.7 Benzo[b]thiophene 101 5.8 Benzo[c]thiophene 104 5.9 2,5-Dihydrothiophene 105 5.10 Thiolane 106 5.11 Selenophene 107 5.12 Pyrrole 108 5.13 Indole 125 5.14 Carbazole 148 5.15 Isoindole 150 5.16 Indolizine 152 5.17 Pyrrolidine 157 5.18 Phosphole 161 5.19 1,3-Dioxolane 162 5.20 1,2-Dithiole 163 5.21 1,2-Dithiolane 164 5.22 1,3-Dithiole 165 5.23 1,3-Dithiolane 165 5.24 Oxazole 166 5.25 Benzoxazole 177 5.26 4,5-Dihydrooxazole 181 5.27 Isoxazole 185 5.28 4,5-Dihydroisoxazole 193 5.29 2,3-Dihydroisoxazole 198 5.30 Thiazole 199 5.31 Benzothiazole 208 5.32 Penam 212 5.33 Isothiazole 214 5.34 Imidazole 217 5.35 Benzimidazole 229 5.36 Imidazolidine 234 5.37 Pyrazole 236 5.38 Indazole 243 5.39 4,5-Dihydropyrazole 246 5.40 Pyrazolidine 249 5.41 1,2,3-, 1,2,4-, 1,3,4-Oxadiazole 249 5.42 1,2,5-Oxadiazole 251 5.43 1,2,3-Thiadiazole 254 5.44 1,2,4-Thiadiazole 256 5.45 1,2,3-Triazole 258 5.46 Benzotriazole 265 5.47 1,2,4-Triazole 268 5.48 Tetrazole 273 References 280 6 Six-Membered Heterocycles 297 6.1 Pyrylium Ion 297 6.2 2H-Pyran 305 6.3 2H-Pyran-2-one 306 6.4 3,4-Dihydro-2H-pyran 313 6.5 Tetrahydropyran 317 6.6 2H-Chromene 319 6.7 2H-Chromen-2-one 321 6.8 1-Benzopyrylium Ion 327 6.9 4H-Pyran 329 6.10 4H-Pyran-4-one 331 6.11 4H-Chromene 335 6.12 4H-Chromen-4-one 336 6.13 Chroman 341 6.14 Pyridine 345 6.15 Pyridones 381 6.16 Quinoline 386 6.17 Isoquinoline 406 6.18 Quinolizinium Ion 420 6.19 Dibenzopyridines 423 6.20 Piperidine 429 6.21 Phosphabenzene 434 6.22 1,4-Dioxin, 1,4-Dithiin, 1,4-Oxathiin 438 6.23 1,4-Dioxane 440 6.24 Oxazines 442 6.25 Morpholine 447 6.26 1,3-Dioxane 449 6.27 1,3-Dithiane 453 6.28 Cepham 455 6.29 Pyridazine 458 6.30 Pyrimidine 463 6.31 Purine 474 6.32 Pyrazine 481 6.33 Piperazine 486 6.34 Pteridine 487 6.35 Benzodiazines 491 6.36 1,2,3-Triazine 501 6.37 1,2,4-Triazine 504 6.38 1,3,5-Triazine 508 6.39 1,2,4,5-Tetrazine 512 References 517 7 Seven-Membered Heterocycles 529 7.1 Oxepin 529 7.2 Thiepin 532 7.3 Azepine 533 7.4 Diazepines 540 References 545 8 Larger Ring Heterocycles 547 8.1 Azocine 547 8.2 Heteronines and Larger-Membered Heterocycles 549 8.3 Tetrapyrroles 551 References 558 9 Problems and Their Solutions 561 References 614 Indices 621
£62.05
Wiley-VCH Verlag GmbH Classics in Total Synthesis III: Further Targets,
Book SynopsisK.C. Nicolaou - Winner of the Nemitsas Prize 2014 in Chemistry Adopting his didactically skillful approach, K.C. Nicolaou compiles in this textbook the important synthetic methods that lead to a complex molecule with valuable properties. He explains all the key steps of the synthetic pathway, highlighting the major developments in blue-boxed sections and contrasting these to other synthetic methods.A wonderful tool for learning and teaching and a must-have for all future and present organic and biochemists.Trade Review"Classics in Total Synthesis III will surely itself become a classic in the literature on the state of the art of contemporary organic synthetic chemistry." (Angewandte Chemie, 2011) Table of ContentsINTRODUCTION: THE ADVANCING FIELD OF TOTAL SYNTHESIS Targets Strategies and Methods Classics in Total Synthesis III TETRODOTOXIN Introduction Kishi's Retrosynthetic Analysis and Strategy Kishi's Total Synthesis Du Bois' Retrosynthetic Analysis and Strategy Du Bois' Total Synthesis Conclusion DISCODERMOLIDE Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion AZASPIRACID-1 Introduction Nicolaou's Retrosynthetic Analysis and Strategy Nicolaou's Total Synthesis Evans' Retrosynthetic Analysis and Strategy Evans' Total Synthesis Conclusion THIOSTREPTON Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion PENTACYCLOANAMMOXIC ACID METHYL ESTER Introduction First-Generation Retrosynthetic Analysis and Strategy First-Generation Total Synthesis Second-Generation Retrosynthetic Analysis and Strategy Second-Generation Total Synthesis Conclusion LITTORALISONE, OSELTAMIVIR (TAMIFLU®), AND HIRSUTELLONE B Introduction Introduction to Littoralisone Total Synthesis of Littoralisone Introduction to Oseltamivir (Tamiflu®) Total Synthesis of Oseltamivir (Tamiflu®) Introduction to Hirsutellone B Total Synthesis of Hirsutellone B Conclusion RUBICORDIFOLIN AND RUBIONCOLIN B Introduction Retrosynthetic Analysis of Rubicordifolin Total Synthesis of Rubicordifolin Retrosyntheticd Analysis of Rubioncolin B Total Synthesis of Rubioncolin B Conclusion CYANTHIWIGINS U AND F Introduction Phillips' Retrosynthetic Analysis and Strategy Phillips' Total Synthesis Stolz' Retrosynthetic Analysis and Strategy Stoltz' Total Synthesis Conclusion STEPHACIDIN B Introduction Myers' Retrosynthetic Analysis and Strategy Meyers' Total Synthesis Baran's Retrosynthetic Analysis and Strategy Baran's Total Synthesis Williams' Retrosynthetic Analysis and Strategy Williams' Total Synthesis Conclusion ABYSSOMICIN C AND ATROP-ABYSSOMICIN C Introduction Sorensen's Retrosynthetic Analysis and Strategy Sorensen's Total Synthesis of Abyssomicin C Nicolaou's Retrosynthetic Analysis and Strategy Nicolaou's Total Synthesis of Abyssomicin C and atrop-Abyssomicin C Conclusion TETRACYCLINE Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion BISANTHRAQUINONE NATURAL PRODUCTS Introduction Retrosynthetic Analysis and Strategy Toward 2,2'-epi-Cytoskyrin A, Rugulosin, and Rugulin Total Synthesis of 2,2'-epi-Cytoskyrin A, Rugulosin, and Rugulin Retrosynthetic Analysis and Strategy Toward Antibiotic BE-43472B Total Synthesis of Antibiotic BE-43472B Conclusion GARSUBELLIN A Introduction Sibasaki and Kanai's Retrosynthetic Analysis and Strategy Shibasaki and Kanai's Total Synthesis Danishefsky's Retrosynthetic Analysis and Strategy Danishefsky's Total Synthesis Conclusion WELWITINDOLINONE A Introduction Baran's Retrosynthetic Analysis and Strategy Barans' Total Synthesis Wood's Retrosynthetic Analysis and Strategy Wood's Total Synthesis Conclusion IEJIMALIDE B Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion KEDARCIDIN CHROMOPHORE AND MADUROPEPTIN CHROMOPHORE Introduction Retrosynthetic Analysis and Strategy for Kedarcidin Chromophore Total Synthesis of Kedarcidin Chromophore Retrosynthetic Analysis and Strategy for Maduropeptin Chromophore Total Synthesis of Maduropeptin Chromophore Conclusion BIYOUYANAGIN A Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion AZADIRACHTIN Introduction Retrosynthetic Analysis and Strategy Synthesis Conclusion RESVERATROL-DERIVED NATURAL PRODUCTS Introduction Snyder's Retrosynthetic Analysis and Strategy for a Collection of Resveratrol-Derived Natural Products Snyder's Total Synthesis of a Collection of Resveratrol-Derived Natural Products Nicolaou and Chen's Retrosynthetic Analysis and Strategy for Hopeahainol A and Hopeanol Nicolaou and Chen's Total Synthesis of Hopeahainol A and Hopeanol Conclusion CHLOROSULFOLIPID CYTOTOXIN Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion SPOROLIDE B Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion 11,11'-DIDEOXYVERTICILLIN A AND CHAETOCIN Introduction Retrosynthetic Analysis and Strategy for 11,11'-Dideoxyverticillin A Total Synthesis of 11,11'-Dideoxyverticillin A Retrosynthetic Analysis and Strategy for Chaetocin Total Synthesis of Chaetocin Conclusion VANNUSAL B Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion HAPLOPHYTINE Introduction Fukuyama and Tokuyama's Retrosynthetic Analysis and Strategy Fukuyama and Tokuyama's Total Synthesis Nicolaou and Chen's Retrosynthetic Analysis and Strategy Nicolaou and Chen's Total Synthesis Conclusion PALAU'AMINE Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion
£73.80
Wiley-VCH Verlag GmbH Classics in Total Synthesis III: Further Targets,
Book SynopsisK.C. Nicolaou - Winner of the Nemitsas Prize 2014 in Chemistry Retaining his excellent, proven approach, world-famous chemist and passionate teacher K.C. Nicolaou compiles here the important strategies and tools employed to construct complex molecules. For a total of 42 syntheses of 25 challenging natural products he explains all the key steps of the synthetic pathway, highlighting the major developments in blue-boxed sections for easier understanding, and contrasting these to other synthetic methods. Similar to its predecessors and completing the trilogy, this textbook analyzes the syntheses in a didactic manner, with several chapters including mini-reviews of key methodologies, and an emphasis on the history, mechanism, scope, and generality of the reactions. In contrast to the first two volumes, this new one features full-color frontispieces.A wonderful tool for learning and teaching and a must-have for all current and future organic and biochemists.Trade Review"Classics in Total Synthesis III will surely itself become a classic in the literature on the state of the art of contemporary organic synthetic chemistry." (Angewandte Chemie, 2011)Table of ContentsINTRODUCTION: THE ADVANCING FIELD OF TOTAL SYNTHESIS Targets Strategies and Methods Classics in Total Synthesis III TETRODOTOXIN Introduction Kishi's Retrosynthetic Analysis and Strategy Kishi's Total Synthesis Du Bois' Retrosynthetic Analysis and Strategy Du Bois' Total Synthesis Conclusion DISCODERMOLIDE Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion AZASPIRACID-1 Introduction Nicolaou's Retrosynthetic Analysis and Strategy Nicolaou's Total Synthesis Evans' Retrosynthetic Analysis and Strategy Evans' Total Synthesis Conclusion THIOSTREPTON Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion PENTACYCLOANAMMOXIC ACID METHYL ESTER Introduction First-Generation Retrosynthetic Analysis and Strategy First-Generation Total Synthesis Second-Generation Retrosynthetic Analysis and Strategy Second-Generation Total Synthesis Conclusion LITTORALISONE, OSELTAMIVIR (TAMIFLU®), AND HIRSUTELLONE B Introduction Introduction to Littoralisone Total Synthesis of Littoralisone Introduction to Oseltamivir (Tamiflu®) Total Synthesis of Oseltamivir (Tamiflu®) Introduction to Hirsutellone B Total Synthesis of Hirsutellone B Conclusion RUBICORDIFOLIN AND RUBIONCOLIN B Introduction Retrosynthetic Analysis of Rubicordifolin Total Synthesis of Rubicordifolin Retrosyntheticd Analysis of Rubioncolin B Total Synthesis of Rubioncolin B Conclusion CYANTHIWIGINS U AND F Introduction Phillips' Retrosynthetic Analysis and Strategy Phillips' Total Synthesis Stolz' Retrosynthetic Analysis and Strategy Stoltz' Total Synthesis Conclusion STEPHACIDIN B Introduction Myers' Retrosynthetic Analysis and Strategy Meyers' Total Synthesis Baran's Retrosynthetic Analysis and Strategy Baran's Total Synthesis Williams' Retrosynthetic Analysis and Strategy Williams' Total Synthesis Conclusion ABYSSOMICIN C AND ATROP-ABYSSOMICIN C Introduction Sorensen's Retrosynthetic Analysis and Strategy Sorensen's Total Synthesis of Abyssomicin C Nicolaou's Retrosynthetic Analysis and Strategy Nicolaou's Total Synthesis of Abyssomicin C and atrop-Abyssomicin C Conclusion TETRACYCLINE Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion BISANTHRAQUINONE NATURAL PRODUCTS Introduction Retrosynthetic Analysis and Strategy Toward 2,2'-epi-Cytoskyrin A, Rugulosin, and Rugulin Total Synthesis of 2,2'-epi-Cytoskyrin A, Rugulosin, and Rugulin Retrosynthetic Analysis and Strategy Toward Antibiotic BE-43472B Total Synthesis of Antibiotic BE-43472B Conclusion GARSUBELLIN A Introduction Sibasaki and Kanai's Retrosynthetic Analysis and Strategy Shibasaki and Kanai's Total Synthesis Danishefsky's Retrosynthetic Analysis and Strategy Danishefsky's Total Synthesis Conclusion WELWITINDOLINONE A Introduction Baran's Retrosynthetic Analysis and Strategy Barans' Total Synthesis Wood's Retrosynthetic Analysis and Strategy Wood's Total Synthesis Conclusion IEJIMALIDE B Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion KEDARCIDIN CHROMOPHORE AND MADUROPEPTIN CHROMOPHORE Introduction Retrosynthetic Analysis and Strategy for Kedarcidin Chromophore Total Synthesis of Kedarcidin Chromophore Retrosynthetic Analysis and Strategy for Maduropeptin Chromophore Total Synthesis of Maduropeptin Chromophore Conclusion BIYOUYANAGIN A Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion AZADIRACHTIN Introduction Retrosynthetic Analysis and Strategy Synthesis Conclusion RESVERATROL-DERIVED NATURAL PRODUCTS Introduction Snyder's Retrosynthetic Analysis and Strategy for a Collection of Resveratrol-Derived Natural Products Snyder's Total Synthesis of a Collection of Resveratrol-Derived Natural Products Nicolaou and Chen's Retrosynthetic Analysis and Strategy for Hopeahainol A and Hopeanol Nicolaou and Chen's Total Synthesis of Hopeahainol A and Hopeanol Conclusion CHLOROSULFOLIPID CYTOTOXIN Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion SPOROLIDE B Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion 11,11'-DIDEOXYVERTICILLIN A AND CHAETOCIN Introduction Retrosynthetic Analysis and Strategy for 11,11'-Dideoxyverticillin A Total Synthesis of 11,11'-Dideoxyverticillin A Retrosynthetic Analysis and Strategy for Chaetocin Total Synthesis of Chaetocin Conclusion VANNUSAL B Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion HAPLOPHYTINE Introduction Fukuyama and Tokuyama's Retrosynthetic Analysis and Strategy Fukuyama and Tokuyama's Total Synthesis Nicolaou and Chen's Retrosynthetic Analysis and Strategy Nicolaou and Chen's Total Synthesis Conclusion PALAU'AMINE Introduction Retrosynthetic Analysis and Strategy Total Synthesis Conclusion
£112.16
Wiley-VCH Verlag GmbH Reactions and Syntheses: In the Organic Chemistry
Book SynopsisThe second edition of this classic text book has been completely revised, updated, and extended to include chapters on biomimetic amination reactions, Wacker oxidation, and useful domino reactions.The first-class author team with long-standing experience in practical courses on organic chemistry covers a multitude of preparative procedures of reaction types and compound classes indispensable in modern organic synthesis. Throughout, the experiments are accompanied by the theoretical and mechanistic fundamentals, while the clearly structured sub-chapters provide concise background information, retrosynthetic analysis, information on isolation and purification, analytical data as well as current literature citations. Finally, in each case the synthesis is labeled with one of three levels of difficulty.An indispensable manual for students and lecturers in chemistry, organic chemists, as well as lab technicians and chemists in the pharmaceutical and agrochemical industries.Table of ContentsC-C BOND FORMATION Nucleophilic Addition to Aldehydes, Ketones, Carboxylic Acid Derivatives (Esters, Anhydrides) and alpha,beta-Unsaturated Carbonyl Compounds; Carbonyl Olefination Alkylation of Aldehydes/Ketones, Carboxylic Acids, and beta-Dicarbonyl Compounds Reactions of the Aldol and Mannich Type Electrophilic and Nucleophilic Acylation Reactions of Alkenes via Carbenium Ions Transition-Metal-Catalyzed Reactions Pericyclic Reactions Radical Reactions OXIDATION AND REDUCTION Epoxidation of C=C Bonds Dihydroxylation of C=C Bonds Oxidation of Alcohols to Carbonyl Compounds Enantioselective Reduction of Ketones Biomimetic Reductive Amination Enantioselective Wacker HETEROCYCLIC COMPOUNDS Three- and Four-Membered Heterocycles Five-Membered Heterocycles Six-Membered Heterocycles Condensed Heterocycles Other Heterocyclic Systems; Heterocyclic Dyes SELECTED NATURAL PRODUCTS Isoprenoids Carbohydrates Amino Acids and Peptides Nucleotides and Oligonucleotides DOMINO REACTIONS Domino Reactions in Synthetic Methodology Domino Reactions in The Synthesis of Alkaloids Domino Reactions in The Synthesis of Isoprenoids Domino Reactions for The Synthesis of Chromans And Dioxins Domino Reactions in The Synthesis of Chiroptical Switches INDEX OF REACTIONS INDEX OF PRODUCTS SUBJECT INDEX
£66.50
Wiley-VCH Verlag GmbH Organic Stereochemistry: Experimental and
Book SynopsisAdopting a novel approach to the topic by combining theoretical knowledge and practical results, this book presents the most popular and useful computational and experimental methods applied for studying the stereochemistry of chemical reactions and compounds. The text is clearly divided into three sections on fundamentals, spectroscopic and computational techniques, and applications in organic synthesis. The first part provides a brief introduction to the field of chirality and stereochemistry, while the second part covers the different methodologies, such as optical rotation, electronic circular dichroism, vibrational circular dicroism, and Raman spectroscopy. The third section then goes on to describe selective examples in organic synthesis, classified by reaction type, i.e. enantioselective, chemoselective and stereoselective reactions. A final chapter on total synthesis of natural products rounds off the book. A valuable reference for researchers in academia and industry working in the field of organic synthesis, computational chemistry, spectroscopy or medicinal chemistry.Table of ContentsPreface IX Acknowledgments XI List of Abbreviations XIII Part I Fundamentals 1 1 Chirality 3 1.1 Introduction 3 1.2 Tetrahedron of Carbon 9 1.2.1 Terpenoids 9 1.2.2 Flavonoids 13 1.2.3 Alkaloids 14 1.2.4 Steroids 16 1.2.5 Glycosides 17 1.2.6 Others 18 1.3 Other Stereogenic Centers 19 1.4 Optical Characteristics 23 1.4.1 Measurement of OR 24 1.4.2 ECD and Its Definition 25 1.4.3 Outline of VCD 26 1.4.4 Outline of ROA 27 References 28 2 Non-optical Method in Configuration Study 31 2.1 13CNMR Spectra 31 2.1.1 NMR and Atomic Structure 31 2.1.2 13C NMR Calculation 32 2.1.3 1HNMR 34 2.1.4 13C NMR Prediction and Conformational Search 34 2.2 X-Ray Diffraction and Mosher Method 41 2.2.1 X-Ray Diffraction 41 2.2.2 Mosher Method 44 2.3 Transition State Energy and Chirality Selectivity 51 2.4 Separation of Chiral Compounds 53 2.4.1 Chiral Organic Bases 53 2.4.2 Chiral Organic Acids 53 2.4.3 Chiral Organic Alcohols 53 2.4.4 Others 54 References 55 Part II Techniques 57 3 Optical Rotation (Rotatory Dispersion, ORD) 59 3.1 Introduction 59 3.2 Quantum Theory 59 3.3 Matrix Model 63 3.3.1 Matrix Basis 65 3.3.2 Explanation of General OR Characteristics 68 3.3.2.1 Sample Calculations 68 3.3.2.2 Calculated Values in Same Series of Compounds 73 3.4 ORD 77 3.5 Application 77 3.5.1 AC Assignment for Mono-Stereogenic Center Compounds 79 3.5.2 Matrix Model Application 80 3.5.3 AC Assignment for Poly-Stereogenic Center Compounds 82 3.5.4 Using ORD Method 83 References 84 4 Electronic Circular Dichroism 87 4.1 Exciton Chirality CD 87 4.2 ECD Characteristics for Chiral Metallic Compounds 92 4.3 Quantum Theory Basis 94 4.4 Principle Using ECD 95 4.5 Application 97 4.5.1 Procedure to Do ECD 97 4.5.2 ECD Application 97 4.5.3 UV Correction 102 References 105 5 Vibrational Circular Dichroism and Raman Optical Activity 107 5.1 Exciton Chirality 108 5.2 Quantum Theory Basis 109 5.2.1 VCD and IR 109 5.2.2 ROA and Raman Scattering 110 5.3 Principles Using VCD and ROA 113 5.4 Application 115 5.4.1 VCD Application 115 5.4.2 ROA Application 124 References 126 6 Combinational Use of Different Methods 129 6.1 Tactics to Select Methods 129 6.1.1 13CNMRMethods 130 6.1.2 OR and ORD 131 6.1.3 Matrix 132 6.1.4 ECD 132 6.1.5 VCD Method 133 6.2 Examples and Discussion 133 6.3 Revised Structures 138 6.3.1 ORD Method 139 6.3.2 Combinational Use of OR and ECD 144 6.3.3 VCD and ECD 146 6.3.4 Comprehensive Use of OR, ECD, and VCD 147 References 160 Part III Reactions 163 7 Enantioselective Reaction 165 7.1 Enantioselective Addition 165 7.1.1 Organic Zn- or Zn-Ti Reagent 165 7.1.2 Organic Cu–Zn, Cu–Li Reagent 169 7.1.3 Organo-Fe Complexes 173 7.1.4 Other Organo-Metallic Complexes 175 7.1.5 Organo-Si Reagents 178 7.2 Enantioselective Reduction 178 7.2.1 Green Chemistry 181 7.3 Enantioselective Oxidation 184 7.4 Prediction of ee Using Calculations 185 7.5 Catalyst Types 189 7.5.1 Amino Alcohols 189 7.5.2 Chiral Ligands Containing N–O Group 190 7.5.3 Chiral Axial Catalysts 191 7.5.4 Solid-Supported Chiral Compounds 192 7.5.5 Spiral Chiral Compounds 193 7.5.6 Asymmetric-Axle-Supported Chiral Catalyst 194 7.5.7 Chiral Shiff-Base Ligands 195 7.5.8 Some Asymmetric Lewis Acids 196 7.5.9 Organic P-Containing Ligands 197 7.6 Three Phenomena 198 7.6.1 Chirality Amplification (Nonlinear Effect) 198 7.6.2 Auto-Self Catalysis 199 7.6.3 Odd–Even Carbon Effect 199 References 201 8 Chemoselective Reaction 205 8.1 Chemoselective Additions 205 8.1.1 Addition to C=O or C=C Groups 205 8.2 Chemoselective Reduction 210 8.3 Chemoselective Oxidation 225 8.4 Other Chemoselective Reactions 231 References 237 9 Stereoselective Reaction 241 9.1 Conformational Study 241 9.2 Effect of Conformation on Reactions 247 9.3 Regioselective Reactions 251 9.4 Diastereoselective Reactions 260 9.4.1 Diastereoselective Additions 260 9.4.2 Other Diastereoselective Reactions 270 9.5 Calculation Using Theoretical Protocol 272 References 277 10 Total Organic Synthesis 279 10.1 Introduction 279 10.2 Retrosynthesis Strategies 279 10.3 Examples in Synthesis 285 10.3.1 (+)-Hirsutene 285 10.3.2 (2R,3S)-Rubiginone A2 and Its Analog 287 10.3.3 (+)-Brefeldin A 290 10.3.4 Malyngamide U and Its AC Reassignment 292 10.3.5 Taxol Derivatives 296 10.3.6 Amphidinolide T2 and Its Derivatives 298 10.3.7 (+)-Vindoline 303 10.4 Calculation in Total Synthesis 306 References 309 Index 313
£112.16
Wiley-VCH Verlag GmbH Click Reactions in Organic Synthesis
Book SynopsisThis book on click reactions to focus on organic synthesis, this reference work describes the click concept and underlying mechanisms as well as the main applications in various fields. As such, the chapters cover green chemical synthesis, metal-free click reactions, synthesis of pharmaceuticals, peptides, carbohydrates, DNA, macrocycles, dendrimers, polymers, and supramolecular architectures. By filling a gap in the market, this is the ultimate reference for synthetic chemists in academia and industry aiming for a fast and simple design and synthesis of novel compounds with useful properties.Table of ContentsList of Contributors XI Preface XV 1 Click Chemistry:Mechanistic and Synthetic Perspectives 1Ramesh Ramapanicker and Poonam Chauhan 1.1 Cycloaddition Click Reactions 2 1.1.1 Azide–Alkyne Huisgen 1,3-Dipolar Cycloaddition 2 1.1.2 Copper-Catalyzed Azide–Alkyne Cycloaddition (CuAAC) Click Reaction 2 1.1.2.1 Mechanism of CuAAC Click Reactions 5 1.1.2.2 Catalysts used for CuAAC Click Reactions 6 1.1.2.3 Ligands used for CuAAC Click Reactions 7 1.1.3 Ruthenium-Catalyzed Azide–Alkyne Cycloaddition (RuAAC) Click Reactions 7 1.1.3.1 Mechanism of RuAAC Click Reactions 8 1.1.4 Strain-Promoted Azide–Alkyne Cycloaddition (SPAAC) Reactions 8 1.1.5 Organocatalytic Triazole Formation 10 1.2 Thiol-Based Click Reactions 12 1.2.1 Radical Click Reactions of Thiols 12 1.2.1.1 Thiol–Ene Radical Click Reaction 12 1.2.1.2 Thiol–Yne Radical Click Reaction 14 1.2.2 Nucleophilic Addition Click Reactions ofThiols 15 1.2.2.1 Thiol–Epoxide Click Reactions 17 1.2.2.2 Thiol–Isocyanate Click Reactions 17 1.2.2.3 Thiol–Michael Addition Click Reactions 18 1.2.2.4 Thiol–Halogen Nucleophilic Substitution Reaction 20 1.3 Miscellaneous Click Reactions 21 References 22 2 Applications of Click Chemistry in Drug Discovery and Development 25Balasubramanian Gopalan and Kalpattu Kuppusamy Balasubramanian 2.1 Introduction 25 2.2 Part A: Application of Click Chemistry to Drug Discovery and Development 25 2.2.1 Carbonic Anhydrase Inhibitors 30 2.2.2 Targeting Onchocerca Volvulus Chitinase-1 (OvCHT1) using the Hydroxytriazole Moiety within a Scaffold Hopping Approach 32 2.2.3 1,2,3-Triaole-Derived Anticancer Agents 34 2.2.3.1 Topoisomerase II Inhibitors 34 2.2.3.2 Histone Deacetylase Inhibitors 36 2.2.3.3 Protein Tyrosine Kinase Inhibitors 38 2.2.3.4 Antimicrotubule Agents 39 2.2.3.5 HSP 90 Inhibitors 40 2.2.3.6 Autophagy-Dependent Apoptosis in CancerTherapy 41 2.2.3.7 Anticancer Activity of 4β-Triazole-Podophyllotoxin 42 2.2.3.8 1,2,3-Triazole-Substituted Oleanolic Acid Derivatives as Anticancer Agents 42 2.2.3.9 Anti-Infective Agents 43 2.2.3.10 1,2,3-Triazole Nucleoside 44 2.2.3.11 1,2,3-Triazole Carbonucleosides 45 2.2.3.12 β-Lactamase Inhibitors as Antibacterial Agents 47 2.2.3.13 1,2,3-Triazole-Linked Carbazoles as Antitubercular Agents 48 2.2.3.14 1,4-Diaryl-Substituted 1,2,3-Traizoles as Antimycobacterial (Mtb) Agents 48 2.2.3.15 1,2,3-Triazole-Adamantylacetamide Hybrids as Antitubercular Agents 50 2.2.3.16 Non-Nucleoside HIV Integrase Inhibitors 50 2.2.3.17 MiscellaneousTherapeutic Segments: 1,2,3-Triazole-Linked Dopamine D3 Receptor (D3R) 53 2.2.3.18 Peptidomimetics: 1,2,3-Triazole as a Disulfide Bond Mimetic 53 2.3 Part B: Synthesis of Triazole-Based Drugs Currently in use 54 2.2.1 Tazobactam 54 2.3.1.1 Synthesis of tazobactam from intermediate 102 55 2.3.1.2 Other reports on Tazobactam synthesis 55 2.3.2 Solithromycin 56 2.3.2.1 Synthesis of Solithromycin 57 2.3.3 Cefatrizine 60 2.3.4 Radezolid 61 2.3.5 Molidustat 63 2.3.5.1 Synthesis of Molidustat 63 2.3.6 Tradipitant 63 2.3.7 Carboxyamidotriazole 66 2.3.8 Rufinamide 66 2.3.8.1 Rufinamide–Novartis Process 66 2.3.8.2 An Efficient Synthesis of Rufinamide 68 2.3.8.3 Continuous-Flow Total Synthesis of Rufinamide 68 References 70 3 Green Chemical Synthesis and Click Reactions 77Maria José Arévalo, Óscar López, and Maria Victoria Gil 3.1 Introduction 77 3.2 Huisgen 1,3-Dipolar Cycloaddition 77 3.2.1 Green Perspectives on Reaction Conditions 78 3.2.1.1 Copper(I) Catalysts 78 3.2.1.2 Copper(I) Complexes with Nitrogen- and Phosphorous-Donating Ligands 79 3.2.1.3 Metalated Reagents as Catalysts 82 3.2.1.4 Immobilized Copper Species 82 3.2.1.5 Copper Nanocatalysis 83 3.2.1.6 Other Metals as Catalysts 84 3.2.1.7 Nonconventional Energy Sources 85 3.2.2 Applications to Synthesis 85 3.2.2.1 Regioselectivity of the Alkyne–Azide Cycloaddition 85 3.2.2.2 Different Substitution Patterns on Triazole 86 3.2.2.3 Strain-Promoted Cycloadditions 87 3.2.2.4 Sulfonyl Azides in Huisgen Cycloaddition 87 3.2.2.5 Synthesis of Vinyl-1,2,3-Triazoless 87 3.2.2.6 Triazole Derivative Ligands for Coordination Chemistry 88 3.2.2.7 Tetrazole Synthesis 88 3.2.2.8 Synthesis of Chiral Triazoles 88 3.2.2.9 Synthesis of Triazoles with Luminescent Properties 89 3.2.2.10 Synthesis of Triazole Libraries 89 3.2.2.11 Synthesis of Phosphorylated Triazoles 89 3.3 Other 1,3-Dipolar Cycloadditions 90 3.4 Atom Economy and Simplicity of Procedures in Multicomponent Reactions 90 3.4.1 Reaction Conditions 91 3.4.1.1 Copper Compounds as Catalysts 91 3.4.1.2 Copper Complexes with Nitrogen- and Phosphorous-Donating Ligands 91 3.4.1.3 Immobilized Copper Species 91 3.4.1.4 Copper Nanocatalysis 92 3.5 Summary and Conclusions 92 References 93 4 Synthesis of Substituted 1,2,3-Triazoles through Organocatalysis 99Kengadarane Anebouselvy and Dhevalapally B. Ramachary 4.1 Introduction 99 4.2 Preformed-Enolate-Based Synthesis of Substituted 1,2,3-Triazoles 101 4.3 Preformed-Enamine-Based Synthesis of Substituted 1,2,3-Triazoles 106 4.4 Synthesis of Substituted 1,2,3-Triazoles via Catalytic Enolate Intermediates 109 4.5 General Mechanistic Aspects of Enolate Route 113 4.6 Synthesis of Substituted 1,2,3-Triazoles via Enamine Intermediates 114 4.7 General Mechanistic Aspects of Enamine Route 123 4.8 Synthesis of Substituted 1,2,3-Triazoles via Iminium Intermediate 123 4.9 Miscellaneous Routes for the Synthesis of 1,2,3-Triazoles 124 4.10 Conclusions 136 Acknowledgments 136 References 137 5 Applications of the Cu-Catalyzed Azide–Alkyne Cycloaddition (CuAAC) in Peptides 141Freek A. B. M. Hoogstede and Floris P. J. T. Rutjes 5.1 Introduction 141 5.2 CuAAC-Mediated Peptide Conjugation Strategies 142 5.3 CuAAC-Mediated Peptide Backbone Modification Strategies 148 5.4 Conclusions 157 References 157 6 Synthesis of Diverse Carbohydrate-Based Molecules using Click Chemistry 161Anoop S. Singh, Kunj B.Mishra, AmritaMishra, and Vinod K. Tiwari 6.1 Introduction 161 6.2 Cu-Catalyzed Click Chemistry in the Synthesis of Diverse Glycoconjugates 162 6.3 Synthesis of Carbohydrate-Based Simple to Complex Macrocycles 181 6.4 Click-Inspired Synthesis of Diverse Neoglycoconjugates 185 6.5 Conclusion and Future Perspective 195 Acknowledgment 196 References 196 7 Azide–Alkyne Click Reaction in Polymer Science 203Joydeb Mandal and S. Ramakrishnan 7.1 Introduction 203 7.2 Linear, Dendritic, and Hyperbranched Polymers 205 7.3 Telechelic and Block Copolymers 220 7.4 Star and Star-Block Polymers 226 7.5 Cyclic Polymers 230 7.6 Side-Chain Clickable Polymers 235 7.7 Cross-linked Polymeric Systems 238 7.8 Porous Organic Polymers 242 7.9 Surface Modification using CuAAC Reaction 244 7.10 Strain-Promoted Click Reaction 247 7.11 Topochemical Azide–Alkyne Cycloaddition (TAAC) Reactions 249 7.12 Summary and Outlook 251 References 251 8 Thiol-Based “Click” Chemistry for Macromolecular Architecture Design 255Weidong Zhang, Kui Chen, and Gaojian Chen 8.1 Introduction 255 8.2 Thiol Chemistry for Macromolecular Architecture Design 256 8.2.1 Linear Polymers 256 8.2.2 Graft and Comb Polymers 258 8.2.3 Star Polymers 261 8.2.4 Cyclic Polymers 263 8.2.5 Dendritic and Hyperbranched Polymers 265 8.2.6 Conjugated and Hybrid Polymers 270 8.3 Conclusion 276 Acknowledgments 284 References 284 9 Synthesis of Macrocycles and Click Chemistry 287Dario Pasini 9.1 Introduction 287 9.1.1 Peptide- and Sugar-Containing Click Macrocycles 289 9.1.2 Click Macrocycles for Anion Binding and Supramolecular Recognition 297 9.1.3 Clicking Macrocycles to form Mechanical Bonds 300 9.1.4 Cyclic Polymers Obtained by the CuAAC Click Reaction 302 9.2 Summary and Conclusions 304 References 304 10 Modifications of Nucleosides, Nucleotides, and Nucleic Acids using Huisgen’s [3+2] Azide–Alkyne Cycloaddition: Opening Pandora’s Box 309Franck Amblard, Ozkan Sari, Sebastien Boucle, Ahmed Khalil, and Raymond F. Schinazi 10.1 Introduction 309 10.1.1 Nucleoside Modifications 309 10.1.1.1 Nucleoside Analogs as Potential Drugs 309 10.1.1.2 Nucleoside Bioconjugates 311 10.2 Nucleotide and Nucleic Acid Modifications 316 10.2.1 “Artificial” DNA 316 10.2.2 Presynthetic Modification DNA 316 10.2.3 Postsynthetic Modification 318 10.3 Conclusion 331 Acknowledgments 332 References 332 Index 337
£118.76
Wiley-VCH Verlag GmbH Sicherer Umgang mit Gefahrstoffen: unter
Book SynopsisWas in den Gesetzeskommentaren nicht zu finden ist, wird mit der Expertise eines ausgewiesenen Fachmanns in diesem Buch erklärt: die praktische Umsetzung jener Gesetze und Verordnungen, die für den täglichen Umgang mit Gefahrstoffen von Bedeutung sind. Alle Rechtsgrundlagen, einschließlich der neuen Einstufungen und Kennzeichnungen der CLP-Verordnung und GHS sowie der wesentlichen Vorschriften der REACH-Verordnung, sind aktuell abgebildet. Dabei werden Neuerungen hervorgehoben und erklärt. Ergänzend wird ein Risikokonzept für krebserregende Stoffe vorgestellt.Seit über zwanzig Jahren das Standardwerk zum betrieblichen Umgang mit Gefahrstoffen - in der fünften komplett überarbeiteten und aktualisierten Auflage mit zusätzlichen Übungsaufgaben und Musterlösungen!Trade Review"Was in den Gesetzeskommentaren nicht zu finden ist, wird mit der Expertise eines ausgewiesenen Fachmanns in diesem Buch erklärt: die praktische Umset¬zung jener Gesetze und Verord¬nungen, die für den täglichen Umgang mit Gefahrstoffen von Bedeutung sind." METALL (06/2018) "Das anschaulich geschriebene Standardwerk bietet praxisbezogenes Wissen über alle Gesetze und Verordnungen beim Umgang mit gefährlichen Stoffen in Ausbildung und Beruf. Die komplett überarbeitete Neuauflage enthält alle wichtigen Änderungen und stellt ergänzend ein Risikokonzept für krebserregende Stoffe vor. Die praktische Umsetzung der Gesetze und Verordnungen, die für den täglichen Umgang mit Gefahrstoffen von Bedeutung sind, wird verständlich erklärt." Allgemeines Ministerialblatt der Bayerischen Staatsregierung (30.05.2018) "Was in den Gesetzeskommentaren nicht zu finden ist, wird mit der Expertise eines ausgewiesenen Fachmanns, in diesem Buch erklärt: die praktische Umsetzung jener Gesetze und Verordnungen, die für den täglichen Umgang mit Gefahrstoffen von Bedeutung sind." CHEManager (08.06.2018) "Die Texte sind anschaulich geschrieben und auch für Nicht-Juristen gut verständlich." Cav - Chemie Produktion Anlagen Verfahren (04/2018) "Herbert Bender führt den Lesen anschaulich in die Grundlagen der Toxikologie ein. Aufnahmewege und schädigende Wirkungen werden gut verständlich dargestellt. Es gelingt ihm, die juristischen Texte leicht verständlich zusammenzufassen und durch Graphiken zu veranschaulichen." ZFP-Zeitung (04/2018) "Das praxisnah geschrieben Werk richtet sich an alle, die mit dem Gefahrstoffrecht zu tun haben und ein Nachschlagewerk für den täglichen Gebrauch suchen." PROCESS (04/2018) "Das Standardwerk 'Sicherer Umgang mit Gefahrstoffen' von Herbert F. Bender bietet praxisbezogenes Wissen über alle Gesetze und Verordnungen beim Umgang mit gefährlichen Stoffen in Ausbildung und Beruf. ? Was in den Gesetzeskommentaren nicht zu finden ist, wird mit der Expertise eines ausgewiesenen Fachmanns in diesem Buch erklärt: die praktische Umsetzung jener Gesetze und Verordnungen, die für den täglichen Umgang mit Gefahrstoffen von Bedeutung sind." Brennstoffspiegel + Mineralölrundschau (04/2018) "Das praxisnah geschriebene Werk richtet sich an alle, die mit dem Gefahrstoffrecht zu tun haben und ein Nachschlagewerk für den täglichen Gebrauch suchen." Pharma-Tec (02/2018) "Allen, die beruflich mit dem Gefahrstoffrecht zu tun haben, wird es eine äußerst nützliche Unterstützung bei ihrer täglichen Arbeit und ein hilfreicher Wegweiser im Dschungel des Gefahrstoffrechtes sein." Lebensmittelchemiker-Mitteilungen (1/2012) "Schon längst ist das Praxisbuch für Studium und Beruf 'Sicherer Umgang mit Gefahrstoffen' ein Standardwerk geworden. Nicht verwunderlich, liefert der 'Bender' doch für Studenten der Chemie oder anderer Naturwissenschaften Fachwissen sowohl im toxikologischen als auch im juristischen Bereich. [...] Der Autor Herbert F. Bender bietet mit seinem Kompendium umfassende und verlässliche Informationen zum Thema." Gefährliche Ladung (März 2011) "Der 'Bender' bietet praxisbezogenes Wissen über alle Gesetze und Verordnungen beim Umgang mit gefährlichen Stoffen in Ausbildung und Beruf. Dabei bleibt der Text gewohnt anschaulich und auch für Nicht-Juristen leicht verständlich." www.umweltjournal.de (11.03.2011) "Das Werk 'Sicherer Umgang mit Gefahrstoffen' aus dem Wiley-VCH-Verlag eignet sich gleichermaßen als Lehrbuch für das Studium und als Nachschlagewerk für den Beruf." Process (März 2011)Table of ContentsGeleitwort v Vorwort zur 5. Auflage xiii Vorwort zur 1. Auflage xv Abkürzungsverzeichnis xvii 1 Wissenschaftliche Grundlagen 1 1.1 Grundlagen der Toxikologie 1 1.1.1 Aufnahmewege 2 1.1.2 Metabolismus 6 1.1.3 Akute Wirkung 8 1.1.4 Wirkung bei wiederholter Applikation 10 1.1.5 Sensibilisierende (allergisierende) Wirkung 12 1.1.6 Entwicklungsschädigende Wirkung 15 1.1.7 Fruchtbarkeitsschädigende Wirkung 17 1.1.8 Krebserzeugende Wirkung 18 1.1.9 Erbgutverändernde bzw. keimzellmutagene Wirkung 27 1.2 Aerosole 29 1.3 Physikalisch-chemische Grundlagen 34 1.3.1 Begriffsdefinitionen, sicherheitstechnische Kenndaten 35 1.4 Fragen zu Kapitel 1 40 Literatur 41 2 Gefahrstoffklassen, Einstufung und Kennzeichnung 43 2.1 Einführung in die Einstufungssysteme 43 2.2 Gefahrenklasse: Physikalische Gefahren 43 2.2.1 Gefahrenklasse: „Explosive Stoffe/Gemische und Erzeugnisse mit Explosivstoffen“ 43 2.2.2 Gefahrenklasse „Entzündbare Gase“ 46 2.2.3 Gefahrenklasse „Aerosole“ 47 2.2.4 Gefahrenklasse „Oxidierende Gase“ 48 2.2.5 Gefahrenklasse „Gase unter Druck“ 49 2.2.6 Gefahrenklasse „Entzündbare Flüssigkeiten“ 49 2.2.7 Gefahrenklasse „Entzündbare Feststoffe“ 51 2.2.8 Gefahrenklasse „Selbstzersetzliche Stoffe und Gemische“ und „Organische Peroxide“ 53 2.2.9 Gefahrenklasse „Pyrophore Flüssigkeiten“ und Gefahrenklasse „Pyrophore Feststoffe“ 56 2.2.10 Gefahrenklasse „Selbsterhitzungsfähige Stoffe und Gemische“ 57 2.2.11 Gefahrenklasse „Stoffe und Gemische, die in Berührung mit Wasser entzündbare Gase entwickeln“ 58 2.2.12 Gefahrenklasse „Oxidierende Flüssigkeiten“ und Gefahrenklasse „Oxidierende Feststoffe“ 59 2.2.13 Gefahrenklasse „Metallkorrosiv“ 60 2.2.14 Ergänzende Gefahrenmerkmale 61 2.3 Gefährliche Eigenschaften: Gesundheitsgefahren 62 2.3.1 Gefahrklasse „Akute Toxizität“ 62 2.3.2 Gefahrklasse „Ätz-, Reizwirkung auf die Haut“ 66 2.3.3 Gefahrklasse „Schwere Augenschädigung/Augenreizung“ 68 2.3.4 Gefahrklasse „Sensibilisierung der Atemwege oder der Haut“ 69 2.3.5 Gefahrenklasse „Keimzellmutagenität“ 70 2.3.6 Gefahrenklasse „Karzinogenität“ 72 2.3.7 Gefahrenklasse „Reproduktionstoxizität“ 75 2.3.8 Gefahrenklasse „Spezifische Zielorgan-Toxizität bei einmaliger Exposition“ 79 2.3.9 Gefahrenklasse „Spezifische Zielorgan-Toxizität bei wiederholter Exposition“ 81 2.3.10 Gefahrenklasse „Aspirationsgefahr“ 82 2.3.11 Ergänzende Gefahrenmerkmale 83 2.4 Gefährliche Eigenschaften: Umweltgefahren 84 2.4.1 Gefahrenklassen „Gewässergefährdend“ 84 2.4.2 Gefahrenklassen „Die Ozonschicht schädigend“ 88 2.5 Einstufung von Stoffen 88 2.5.1 Allgemeine Grundsätze 88 2.5.2 Einstufung nach Anhang VI der CLP-Verordnung 89 2.5.3 Einstufung nach dem Einstufungsund Kennzeichnungsverzeichnis 90 2.5.4 Einstufung nach dem Definitionsprinzip 92 2.6 Einstufung von Gemischen 93 2.6.1 Allgemeine Einstufungsregeln 93 2.6.2 Einstufung nicht additiver Eigenschaften 95 2.6.3 Einstufung additiver Eigenschaften 95 2.7 Kennzeichnung gefährlicher Stoffe und Gemische 99 2.7.1 Allgemeine Kennzeichnungsvorschriften 99 2.7.2 Spezielle Kennzeichnungsvorschriften 101 2.8 Fragen zu Kapitel 2 102 Literatur 105 3 Grenzwerte 107 3.1 Arbeitsplatzgrenzwerte 109 3.2 Akzeptanz-, Toleranzkonzentration 111 3.3 MAK-Werte 114 3.4 Luftgrenzwerte der EU 117 3.5 DNEL-/DMEL-Werte 119 3.6 Grenzwerte im biologischen Material 120 3.6.1 Der biologische Grenzwert 120 3.6.2 Biologischer Arbeitsplatztoleranzwert 121 3.6.3 Stoffspezifische Äquivalenzwerte im biologischem Material für krebserzeugende Stoffe 123 3.7 Fragen zu Kapitel 3 124 Literatur 126 4 Das Chemikaliengesetz und Arbeitsschutzregelungen 127 4.1 Einführung in das nationale und europäische Rechtssystem 127 4.2 Das Chemikaliengesetz 130 4.2.1 Aufbau des Chemikaliengesetzes 130 4.2.2 Anwendungsbereich 131 4.2.3 Durchführung der EU-REACH-Verordnung 131 4.2.4 Durchführung der EU-Biozidverordnung 132 4.2.5 Mitteilungspflichten bei Gemischen 136 4.2.6 Ermächtigungsgrundlagen 137 4.2.7 Verordnungen des Chemikaliengesetzes 137 4.3 Die Gefahrstoffverordnung 137 4.3.1 Zielsetzung, Anwendungsbereich und Begriffsbestimmungen 138 4.3.2 Vorschriften beim Inverkehrbringen 141 4.3.3 Informationsermittlung und Gefährdungsbeurteilung 142 4.3.4 Grundpflichten 145 4.3.5 Allgemeine Schutzmaßnahmen nach § 8 147 4.3.6 Zusätzliche Schutzmaßnahmen nach § 9 149 4.3.7 Besondere Schutzmaßnahmen bei Tätigkeiten mit krebserzeugenden, keimzellmutagenen und reproduktionstoxischen Gefahrstoffen 150 4.3.8 Besondere Schutzmaßnahmen bei physikalisch-chemischer Einwirkung 151 4.3.9 Betriebsstörungen, Unfälle und Notfälle 152 4.3.10 Unterrichtung und Unterweisung der Beschäftigten 152 4.3.11 Zusammenarbeit verschiedener Firmen 156 4.3.12 Herstellungs- und Verwendungsbeschränkungen 157 4.4 Die Anhänge der Gefahrstoffverordnung 157 4.4.1 Anhang I: Besondere Vorschriften für bestimmte Gefahrstoffe und Tätigkeiten 158 4.4.2 Anhang II: Besondere Herstellungs- und Verwendungsbeschränkungen für bestimmte Stoffe, Gemische und Erzeugnisse 162 4.4.3 Anhang III: Spezielle Anforderungen an Tätigkeiten mit organischen Peroxiden 163 4.5 Lagerung von Gefahrstoffen in ortsbeweglichen Behältern 164 4.5.1 Anwendungsbereich 164 4.5.2 Aufbau und Schutzmaßnahmen 167 4.5.3 Zusammenlagerungskonzept 169 4.6 Mutterschutzverordnung und Jugendarbeitsschutzgesetz 172 4.7 EG-Agenzienrichtlinie 173 4.8 EG-Krebsrichtlinie 174 4.9 Fragen zu Kapitel 4 176 Literatur 180 5 Reach 183 5.1 Anwendungsbereich 185 5.2 Begriffsbestimmungen 186 5.3 Die Registrierung 187 5.3.1 Allgemeine Registrieranforderungen 188 5.3.2 Mengenabhängige Registrieranforderungen 190 5.3.3 Stoffsicherheitsbericht 191 5.3.4 Forschung und Entwicklung 193 5.3.5 Zwischenprodukte 195 5.4 Das Zulassungsverfahren 196 5.5 Informationen in der Lieferkette 203 5.6 Das Sicherheitsdatenblatt 204 5.7 Das erweiterte Sicherheitsdatenblatt 208 5.8 Verbote beim Inverkehrbringen 210 5.9 Fragen zu Kapitel 5 210 Literatur 212 6 Abgabeverbote und Beschränkungen 213 6.1 Verbote und Beschränkungen nach Anhang XVII der REACH-Verordnung 213 6.2 Chemikalien-Verbotsverordnung 222 6.2.1 Verbote und Beschränkungen beim Inverkehrbringen 223 6.2.2 Vorschriften bei der Abgabe bestimmter Stoffe/Gemische 225 6.2.3 Abgabe an den privaten Endverbraucher 227 6.2.4 Abgabe an berufsmäßige Verwender 229 6.2.5 Sachkunde 231 6.2.6 Straftaten, Ordnungswidrigkeiten 232 6.3 Fragen zu Kapitel 6 233 Literatur 239 7 Weitere Stoffgesetze 241 7.1 Das Pflanzenschutzgesetz 242 7.1.1 Kennzeichnung von Pflanzenschutzmitteln 245 7.1.2 Sachkundeerfordernis 247 7.1.3 Abgabe von Pflanzenschutzmitteln 248 7.2 Das Wasserhaushaltsgesetz 249 7.3 Das Kreislaufwirtschafts- und Abfallgesetz 250 7.4 Das Gefahrgutgesetz 252 7.5 Stoffkunde 254 7.6 Erste Hilfe 257 7.7 Fragen zu Kapitel 7 258 Literatur 261 Antworten zu den Aufgaben 263 Stichwortverzeichnis 265
£40.50
Wiley-VCH Verlag GmbH C-H Activation for Asymmetric Synthesis
Book SynopsisProvides, in one handbook, comprehensive coverage of one of the hottest topics in stereoselective chemistry Written by leading international authors in the field, this book introduces readers to C-H activation in asymmetric synthesis along with all of its facets. It presents stereoselective C-H functionalization with a broad coverage, from outer-sphere to inner-sphere C-H bond activation, and from the control of olefin geometry to the induction of point, planar and axial chirality. Moreover, methods wherein asymmetry is introduced either during the C-H activation or in a different elementary step are discussed. Presented in two parts?asymmetric activation of C(sp3)-H bonds and stereoselective synthesis implying activation of C(sp2)-H bonds?CH-Activation for Asymmetric Synthesis showcases the diversity of stereogenic elements, which can now be constructed by C-H activation methods. Chapters in Part 1 cover: C(sp3)-H bond insertion by metal carbenoids and nitrenoids; stereoselective C-C bond and C-N bond forming reactions through C(sp3)?H bond insertion of metal nitrenoids; enantioselective intra- and intermolecular couplings; and more. Part 2 looks at: C-H activation involved in stereodiscriminant step; planar chirality; diastereoselective formation of alkenes through C(sp2)?H bond activation; amongst other methods. -Covers one of the most rapidly developing fields in organic synthesis and catalysis -Clearly structured in two parts (activation of sp3- and activation of sp2-H bonds) -Edited by two leading experts in C-H activation in asymmetric synthesis CH-Activation for Asymmetric Synthesis will be of high interest to chemists in academia, as well as those in the pharmaceutical and agrochemical industry. Table of ContentsForeword xi Part I Asymmetric Activation of C(sp3)—H Bonds 1 Part I.A C(sp3)—H Bond Insertion by Metal Carbenoids and Nitrenoids 2 1 Stereoselective C—C Bond-Forming Reactions Through C(sp3)—H Bond Insertion of Metal Carbenoids 3 Aoife M. Buckley, Thomas A. Brouder, Alan Ford, and Anita R. Maguire 1.1 Introduction 3 1.2 Diazo Compounds 4 1.3 Mechanistic Understanding 5 1.4 Catalysts 7 1.4.1 Copper 7 1.4.1.1 Bisoxazoline and Schiff Base 7 1.4.2 Rhodium 8 1.4.2.1 Rhodium(II) Carboxylates 9 1.4.2.2 Rhodium(II) Carboxamidates 10 1.4.2.3 Ortho-metalated Complexes 11 1.4.3 Iridium and Ruthenium 11 1.5 Intramolecular C(sp3)—H Bond Insertion 11 1.5.1 Chemoselectivity 13 1.5.1.1 Catalyst Effects 13 1.5.1.2 Substrate Effects 14 1.5.2 Regioselectivity 16 1.5.2.1 Formation of Three-Membered Rings 17 1.5.2.2 Formation of Four-Membered Rings 18 1.5.2.3 Formation of Five-Membered Rings 20 1.5.2.4 Formation of Six-Membered Rings 20 1.5.3 Diastereoselectivity 23 1.5.3.1 Substrate Effects 23 1.5.3.2 Catalyst Effects 25 1.5.4 Enantioselectivity 25 1.6 Intermolecular C(sp3)—H Bond Insertion 30 1.6.1 Chemoselectivity 30 1.6.1.1 Diazo Compounds 32 1.6.1.2 Catalyst Effects 34 1.6.1.3 Substrate Functional Groups 35 1.6.2 Regioselectivity 36 1.6.2.1 Substrate Effects 36 1.6.2.2 Catalyst Effects 38 1.6.2.3 Diazo Compound Effects 39 1.6.3 Diastereoselectivity 39 1.6.3.1 Substrate Effects 39 1.6.3.2 Catalyst Effects 42 1.6.4 Enantioselectivity 43 1.7 Conclusion 45 References 45 2 Stereoselective C—N Bond-Forming Reactions Through C(sp3)—H Bond Insertion of Metal Nitrenoids 51 Philippe Dauban, Romain Rey-Rodriguez, and Ali Nasrallah 2.1 Introduction 51 2.2 Historical Background 52 2.2.1 Seminal Studies in Catalytic C(sp3)–H Amination 52 2.2.2 Mechanistic and Stereochemical Issues 56 2.3 Catalytic Stereoselective C(sp3)–H Amination Reactions with Iminoiodinanes 60 2.3.1 Catalytic Intermolecular Enantioselective Reactions (Chirality Only on the Metal Complex) 60 2.3.2 Catalytic Intramolecular Enantioselective Reactions 63 2.3.3 Catalytic Intermolecular Diastereoselective Reactions (Chirality on the Metal Complex and the Nitrene Precursor) 66 2.4 Catalytic Stereoselective C(sp3)–H Amination Reactions with Azides 67 2.4.1 Transition Metal-Catalyzed C(sp3)–H Amination Reactions 67 2.4.2 Enzymatic C(sp3)–H Amination Reactions 68 2.5 Catalytic Stereoselective C(sp3)–H Amination Reactions with N-(Sulfonyloxy)carbamates 70 2.6 Conclusion 72 References 72 Part I.B C(sp3)–H Activation as Stereodiscriminant Step 77 3 Enantioselective Intra- and Intermolecular Couplings 79 Qiaoqiao Teng and Wei-Liang Duan 3.1 Introduction 79 3.2 Enantioselective Intramolecular Couplings of Aliphatic Substrates 79 3.2.1 C–C Coupling 79 3.2.2 C–X Coupling 89 3.3 Enantioselective Intermolecular Couplings of Aliphatic Substrates 90 3.3.1 Pd Catalysis 91 3.3.2 Rh Catalysis 102 3.3.3 Ir Catalysis 102 3.4 Conclusion 104 References 105 4 Substrate-Controlled Transformation: Diastereoselective Functionalization 107 Sheng-Yi Yan, Bin Liu, and Bing-Feng Shi 4.1 Introduction 107 4.2 Diastereoselective Functionalizations of N-Phthaloyl-α-Amino Acids 108 4.2.1 Diastereoselective β-C(sp3)–H Functionalizations of N-Phthaloyl-α-Amino Acids 108 4.2.1.1 Bidentate Directing Group 108 4.2.1.2 Monodentate Directing Group 114 4.2.2 Diastereoselective γ-C(sp3)–H Functionalization of α-Amino Acid Derivatives 114 4.3 Diastereoselective C–H Activation Controlled by Chiral Auxiliary 116 4.4 Diastereoselective C(sp3)–H Functionalization of Conformationally Restricted Cyclic Substrates 121 4.5 Summary and Conclusions 127 References 128 Part II Stereoselective Synthesis Implying Activation of C(sp2)—H Bonds 131 5 Planar Chirality via C(sp2)–H Activation Involved in Stereodiscriminant Step 133 Qing Gu and Shu-Li You 5.1 Introduction 133 5.2 Diastereoselective Synthesis of Planar Chiral Ferrocenes 134 5.3 Enantioselective Synthesis of Planar Chiral Ferrocenes 134 5.3.1 Pd(II)-Catalyzed Direct C—H Bond Functionalization 134 5.3.2 Pd(0)-Catalyzed Direct C—H Bond Functionalization 140 5.3.3 Ir/Rh-Catalyzed Direct C—H Bond Functionalization 144 5.3.4 Au/Pt-Catalyzed Direct C—H Bond Functionalization 146 5.4 Conclusion 147 References 148 6 Axial Chirality via C(sp2)–H Activation Involved in Stereodiscriminant Step 151 Quentin Dherbassy, Joanna Wencel-Delord, and Françoise Colobert 6.1 Introduction 151 6.2 Asymmetric Coupling of Two Arenes by Oxidative Dimerization 152 6.2.1 Copper-Catalyzed Reactions 153 6.2.2 Vanadium-Catalyzed Reactions 154 6.2.3 Iron-Catalyzed Reactions 155 6.2.4 Application in the Synthesis of Natural Products 155 6.2.5 Conclusion 156 6.3 Stereoselective C–H Functionalization of Prochiral or Racemic Biaryls 158 6.3.1 Asymmetric C–H Alkylation of Naphthylpyridines 158 6.3.2 Diastereoselective C–H Functionalization Using a Chiral Directing Group 159 6.3.2.1 Sulfinyl as Chiral Directing Group 159 6.3.2.2 Phosphates as Chiral Directing Group 162 6.3.3 Enantioselective C–H Functionalization of Racemic Biaryl 163 6.3.4 Stereoselective C–H Functionalization Using a Transient Chiral Directing Group 165 6.3.5 Conclusion 167 6.4 Atroposelective Cross-Coupling of Two Moieties 167 6.4.1 Pd-Catalyzed C–H Arylation of Thiophene Derivatives 167 6.4.2 Pd-Catalyzed C–H Arylation of Biaryl Sulfoxides 169 6.4.3 Rh-Catalyzed C–H Arylation of Diazonaphthoquinones 171 6.4.4 Conclusion 172 6.5 General Conclusion 172 References 172 7 Central Chirality via Asymmetric C(sp2)–H Activation Implying Desymmetrization and Kinetic Resolution 175Soufyan Jerhaoui, Françoise Colobert, and Joanna Wencel-Delord 7.1 Synthesis of C-Stereogenic Molecules via C(sp2)–H Functionalization 175 7.1.1 Desymmetrization 175 7.1.2 Kinetic Resolution 182 7.2 Synthesis of P-Central Chiral Molecules via C(sp2)–H Functionalization 183 7.3 Synthesis of Chiral Organosilicon Molecules via C(sp2)–H Functionalization 187 7.4 Synthesis of S-Chiral Molecules via C(sp2)–H Functionalization 189 7.5 Conclusions 190 References 191 8 Non-stereoselective C(sp2)–H Activation Followed by Selective Functionalization of Metallacyclic Intermediate 193 Xiaohong Chen, Xue Gong, Bo Wang, and Guoyong Song 8.1 Introduction 193 8.2 Intramolecular Couplings 194 8.2.1 Palladium and Nickel Catalysis 194 8.2.2 Rhodium Catalysis 196 8.2.3 Iridium Catalysis 200 8.2.4 Enantioselective Hydroacylation 203 8.3 Intermolecular Couplings 210 8.3.1 Rhodium Catalysis 210 8.3.2 Iridium Catalysis 219 8.3.3 Other Metal Catalysis 226 8.4 Conclusion 231 Acknowledgments 231 References 231 9 Diastereoselective Formation of Alkenes Through C(sp2)—H Bond Activation 239 Parthasarathy Gandeepan and Lutz Ackermann 9.1 Introduction 239 9.2 C–H Activation with Alkenes 241 9.2.1 Nondirected C–H Alkenylation 241 9.2.2 Directed C–H Alkenylation 244 9.3 C–H Activation with Alkenyl (Pseudo)halides 250 9.4 Hydroarylation 252 9.4.1 Hydroarylation of Alkynes 252 9.4.2 Hydroarylation of Allenes 257 9.5 Hydroacylation 261 9.5.1 Hydroacylation of Alkynes 261 9.5.2 Hydroacylation of Allenes 263 9.6 Conclusion 264 References 265 Index 275
£108.86
