Description
Book SynopsisCarbocation chemistry is not only fundamental to the advancement of organic chemistry, it also has found widespread applications in organic synthesis. It is not an exaggeration to say that carbocation chemistry is part of the foundation of organic chemistry.
Carbocation Chemistry: Applications in Organic Synthesis provides a panoramic view of carbocation chemistry with an emphasis on synthetic applications.
This book is an invaluable tool for organic, medicinal and analytical chemists, including those working in biochemistry as well as the petroleum, plastics and pharmaceutical industries. It is also suitable for upper level undergraduates and graduates in organic chemistry, biochemistry and medicinal chemistry.
Table of ContentsChapter 1. Introduction
- Nomenclature, Structure, and Stability
- Generation of Carbocations
- The Non-Classical Ion Controversy
- Electrophilic Addition to Alkenes
- Electrophilic Aromatic Substitution
- Elimination reactions
- Rearrangement Reactions of Carbocations
- References
Chapter 2. Nucleophilic Aliphatic Substitution – SN1
- Introduction
- -Activated Alcohols—Brønsted Acids
- -Activated Alcohols—Lewis Acids
- Alkylation of Aldehydes and Ketones
- Glycosylation
- Friedel–Crafts Alkylation and Acylation
- Electrophilic Fluorination Using Fluoronium Ion
- Miscellaneous SN1-related Reactions
- References
Chapter 3. Nucleophilic Aliphatic Substitution – SN2
- Construction of Quaternary Stereogenic Centers
- Sulfur Chemistry
- Organometallic Chemistry
- Macrocyclization
- Glycosylation
- Nucleoside Analogues
- N-Alkylation
- Cyclotetraphosphazenes
- Conformationally Locked Tetrahydropyran Ring
- The Ionic Liquid Effect
- Silver Chemistry
- References
Chapter 4. Electrophilic Addition to Alkenes
- Introduction
- Cyclopropanation
- Hydroboration/Oxidation
- The Pauson–Khand Reaction
- Prins Reaction
- Schmidt Reaction
- Halogenation
- Oxymercuration/Reduction
- Epoxidation
- Gold-Catalyzed Alkyne Hydration
- Conclusion
- References
Chapter 5. Electrophilic Aromatic Substitution
- Introduction
- Nitration
- Halogenation
- Friedel–Crafts Alkylation
- Friedel–Crafts Acylation
- Applications of Friedel–Crafts Reaction on Total Synthesis
- Miscellaneous Electrophilic Aromatic Substitution Reactions
- References
Chapter 6. Fragmentation and Rearrangement Reactions
- Claisen Rearrangements
- Cope Rearrangements
- Cope Rearrangements
- Aldehyde (or Ketone) Formation Rearrangements
- Carboxylic Acid Formation Rearrangements
- Alcohol Formation Rearrangements
- Amine Formation Rearrangement
- Amides
- Hydrocarbon Rearrangements
- Oxacyclic, Carbocyclic, Oxazoles, Tetrahydrapuran and Tetrahydropuran Formation Rearrangements
- Rearrangements resulting in less common functional groups
- Fragmentations
- References
