{"product_id":"the-chemistry-of-123thiadiazoles-volume-62-9780471326625","title":"The Chemistry of 123Thiadiazoles Volume 62","description":"\u003cb\u003eBook Synopsis\u003c\/b\u003e\u003cbr\u003e1,2,3-Thiadiazoles are a group of heterocycles whose derivatives are important in industry, medicine, and agriculture. This volume provides a complete treatment of this group of heterocycles with an emphasis on syntheses, structural data, properties, reactions, and applications.\u003cbr\u003e\u003cbr\u003e\u003cb\u003eTable of Contents\u003c\/b\u003e\u003cbr\u003e\u003cp\u003e\u003cb\u003e1 Synthesis of 1,2,3-thiadiazoles 1\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e1.1 Cyclization of Hydrazones with Thionyl Chloride (Hurd–Mori Synthesis) 1\u003c\/p\u003e \u003cp\u003e1.1.1 Scope and Limitations 2\u003c\/p\u003e \u003cp\u003e1.1.2 Mechanism of the Hurd–Mori Reaction 4\u003c\/p\u003e \u003cp\u003e1.1.3 Application of the Hurd–Mori Reaction in Organic Synthesis 5\u003c\/p\u003e \u003cp\u003e1.2 Cycloaddition of Diazoalkanes onto a C=S bond (Pechmann Synthesis) 17\u003c\/p\u003e \u003cp\u003e1.3 Heterocyclization of α-diazo Thiocarbonyl Compounds (Wolff Synthesis) 22\u003c\/p\u003e \u003cp\u003e1.3.1 Introduction of a Diazo Function into Compounds Containing a C=S Bond 23\u003c\/p\u003e \u003cp\u003e1.3.2 Introduction of a C=S Bond in the α-position to a Diazo Group 27\u003c\/p\u003e \u003cp\u003e1.3.3 Simultaneous Introduction of Diazo and Thiocarbonyl Functions 29\u003c\/p\u003e \u003cp\u003e1.4 Transformations of other Sulfur-containing Heterocyclic Compounds 30\u003c\/p\u003e \u003cp\u003e1.5 Elaboration of Preformed 1,2,3-Thiadiazoles 33\u003c\/p\u003e \u003cp\u003e1.5.1 Carboxylic Acids 33\u003c\/p\u003e \u003cp\u003e1.5.2 Functional Derivatives of Carboxylic Acids 35\u003c\/p\u003e \u003cp\u003e1.5.3 Aldehydes 36\u003c\/p\u003e \u003cp\u003e1.5.4 Amino-1,2,3-Thiadiazoles 37\u003c\/p\u003e \u003cp\u003e1.5.5 Halo Derivatives 39\u003c\/p\u003e \u003cp\u003e1.5.6 5-Hydrazino-, 5-Mercapto-1,2,3-Thiadiazoles and 5-Sulfide Derivatives 40\u003c\/p\u003e \u003cp\u003e1.5.7 2-(1,2,3-Thiadiazol-5-yl)acetic Acid Derivatives 41\u003c\/p\u003e \u003cp\u003e1.5.8 Alkenyl-1,2,3-Thiadiazoles 42\u003c\/p\u003e \u003cp\u003e1.5.9 5-Hydroxyiminomethyl- and 5-Diazomethyl-1,2,3-Thiadiazoles 42\u003c\/p\u003e \u003cp\u003e1.5.10 4-Hydroxymethyl-1,2,3-Thiadiazoles 43\u003c\/p\u003e \u003cp\u003e1.6 Tables 44\u003c\/p\u003e \u003cp\u003e1.7 Selected Procedures 79\u003c\/p\u003e \u003cp\u003e1.7.1 1,2,3-Thiadiazole-4-Carbaldehyde 79\u003c\/p\u003e \u003cp\u003e1.7.2 4-Phenyl-1,2,3-Thiadiazole 80\u003c\/p\u003e \u003cp\u003e1.7.3 4-Phenyl-1,2,3-Thiadiazole-5-Carbaldehyde 81\u003c\/p\u003e \u003cp\u003e1.7.4 4-Phenyl-5-Oxyiminomethyl-1,2,3-Thiadiazole 82\u003c\/p\u003e \u003cp\u003e1.7.5 5-Phenyl-1,2,3-Thiadiazole-4-Carbaldehyde 82\u003c\/p\u003e \u003cp\u003e1.7.6 5-Chloro-1,2,3-Thiadiazole-4-Carbaldehyde 83\u003c\/p\u003e \u003cp\u003e1.7.7 Ethyl 5-amino-1,2,3-Thiadiazole-4-Carboxylate 84\u003c\/p\u003e \u003cp\u003e1.7.7.1 Pechmann Method 84\u003c\/p\u003e \u003cp\u003e1.7.7.2 Wolff Method 85\u003c\/p\u003e \u003cp\u003e1.7.8 Ethyl 5-chloro-1,2,3-Thiadiazole-4-Carboxylate 86\u003c\/p\u003e \u003cp\u003e1.7.9 4-Phenyl-2-(2,4,6-Trichlorophenyl)-1,2,3-Thiadiazolium Chloride 86\u003c\/p\u003e \u003cp\u003e1.7.10 5-Amino-4-ethoxycarbonyl-2-phenyl-1,2,3-thiadiazolium bromide 87\u003c\/p\u003e \u003cp\u003eReferences 88\u003c\/p\u003e \u003cp\u003e\u003cb\u003e2 Structure of 1,2,3-Thiadiazoles 93\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e2.1 Theoretical Methods 93\u003c\/p\u003e \u003cp\u003e2.2 Experimental Structural Methods 97\u003c\/p\u003e \u003cp\u003e2.2.1 X-ray Analysis 97\u003c\/p\u003e \u003cp\u003e2.2.2 Nuclear Magnetic Resonance Spectroscopy 103\u003c\/p\u003e \u003cp\u003e2.2.2.1 Proton NMR Spectroscopy 103\u003c\/p\u003e \u003cp\u003e2.2.2.2 Carbon-13 NMR Spectroscopy 103\u003c\/p\u003e \u003cp\u003e2.2.2.3 Nitrogen-14 NMR Spectroscopy 106\u003c\/p\u003e \u003cp\u003e2.2.2.4 Nitrogen-15 NMR Spectroscopy 106\u003c\/p\u003e \u003cp\u003e2.2.3 Mass Spectrometry 107\u003c\/p\u003e \u003cp\u003e2.2.4 Other Spectroscopic Data 110\u003c\/p\u003e \u003cp\u003eReferences 110\u003c\/p\u003e \u003cp\u003e\u003cb\u003e3 Chemical Properties of 1,2,3-Thiadiazoles 113\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e3.1 Reactions due to the Reactivity of Ring Atoms 113\u003c\/p\u003e \u003cp\u003e3.1.1 Reactions with Electrophiles 113\u003c\/p\u003e \u003cp\u003e3.1.1.1 Protonation 113\u003c\/p\u003e \u003cp\u003e3.1.1.2 Complexation 114\u003c\/p\u003e \u003cp\u003e3.1.1.3 Alkylation 115\u003c\/p\u003e \u003cp\u003e3.1.1.4 Acylation 116\u003c\/p\u003e \u003cp\u003e3.1.1.5 Oxidation 116\u003c\/p\u003e \u003cp\u003e3.1.1.6 Electrophilic Substitution of Hydrogen 117\u003c\/p\u003e \u003cp\u003e3.1.2 Reactions with Nucleophiles 117\u003c\/p\u003e \u003cp\u003e3.1.2.1 Attack at the Sulfur Atom 117\u003c\/p\u003e \u003cp\u003e3.1.2.2 Attack at the C\u003csub\u003e5\u003c\/sub\u003e Atom 118\u003c\/p\u003e \u003cp\u003e3.1.2.3 Attacks at H\u003csub\u003e4\u003c\/sub\u003e and H\u003csub\u003e5\u003c\/sub\u003e 120\u003c\/p\u003e \u003cp\u003e3.1.2.4 Cycloaddition Reactions 121\u003c\/p\u003e \u003cp\u003e3.2 Reactions of Substituents 122\u003c\/p\u003e \u003cp\u003e3.2.1 5-Alkyl-1,2,3-thiadiazoles 122\u003c\/p\u003e \u003cp\u003e3.2.2 1,2,3-Thiadiazole-4-carbaldehyde 123\u003c\/p\u003e \u003cp\u003e3.2.3 5-Amino-1,2,3-thiadiazole-4-carbothioamide 124\u003c\/p\u003e \u003cp\u003e3.2.4 Mercapto-1,2,3-thiadiazoles 124\u003c\/p\u003e \u003cp\u003e3.3 Rearrangements 124\u003c\/p\u003e \u003cp\u003e3.3.1 Dimroth-type Rearrangements 125\u003c\/p\u003e \u003cp\u003e3.3.2 Cornforth-type Rearrangements 129\u003c\/p\u003e \u003cp\u003e3.3.2.1 Rearrangements of 4-(iminomethyl)- substituted-1,2,3-Thiadiazoles 129\u003c\/p\u003e \u003cp\u003e3.3.2.2 Degenerate Rearrangements of 4-Thiocarbamoyl-1,2,3-Thiadiazoles 133\u003c\/p\u003e \u003cp\u003e3.3.2.3 Rearrangements of 1,2,3-Thiadiazoles Bearing Diazo, Azido and Hydrazono Groups in the 5-`Position 133\u003c\/p\u003e \u003cp\u003e3.3.2.4 Tandem Rearrangements 136\u003c\/p\u003e \u003cp\u003e3.4 Ring Cleavage of 1,2,3-Thiadiazoles 137\u003c\/p\u003e \u003cp\u003e3.4.1 Thermal Decomposition 137\u003c\/p\u003e \u003cp\u003e3.4.2 Photochemical Decomposition 141\u003c\/p\u003e \u003cp\u003e3.4.3 Base-catalyzed Decomposition 143\u003c\/p\u003e \u003cp\u003e3.4.4 Oxidative and Reductive Processes 149\u003c\/p\u003e \u003cp\u003e3.4.5 Other Processes for Ring Cleavage 151\u003c\/p\u003e \u003cp\u003eReferences 152\u003c\/p\u003e \u003cp\u003e\u003cb\u003e4 Fused 1,2,3-Thiadiazoles 155\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e4.1 1,2,3-Thiadiazoles Fused with Five-Membered Rings 155\u003c\/p\u003e \u003cp\u003e4.1.1 Cyclopenteno-1,2,3-thiadiazoles 155\u003c\/p\u003e \u003cp\u003e4.1.2 Pyrrolo[2,3-d][1,2,3]thiadiazoles 158\u003c\/p\u003e \u003cp\u003e4.1.3 Pyrrolo[3,2-d][1,2,3]thiadiazoles 158\u003c\/p\u003e \u003cp\u003e4.1.4 Pyrrolo[3,4-d][1,2,3]thiadiazoles 158\u003c\/p\u003e \u003cp\u003e4.1.5 4,6-Dihydrofurano[3,4-d][1,2,3]thiadiazoles 159\u003c\/p\u003e \u003cp\u003e4.1.6 Thieno[2,3-d][1,2,3]thiadiazoles 159\u003c\/p\u003e \u003cp\u003e4.1.7 Thieno[3,2-d][1,2,3]thiadiazoles 160\u003c\/p\u003e \u003cp\u003e4.1.8 Thieno[3,4-d][1,2,3]thiadiazoles 162\u003c\/p\u003e \u003cp\u003e4.1.9 Selenopheno[3,4-d][1,2,3]thiadiazole 162\u003c\/p\u003e \u003cp\u003e4.1.10 Benzoselenopheno[3,2-d][1,2,3]thiadiazole 163\u003c\/p\u003e \u003cp\u003e4.2 1,2,3-Thiadiazoles Fused with Six-Membered Rings 163\u003c\/p\u003e \u003cp\u003e4.2.1 Cyclohexeno-1,2,3-thiadiazoles 163\u003c\/p\u003e \u003cp\u003e4.2.2 Benzo-1,2,3-thiadiazoles 166\u003c\/p\u003e \u003cp\u003e4.2.3 Piperidino[3,4-d][1,2,3]thiadiazoles 173\u003c\/p\u003e \u003cp\u003e4.2.4 1,2,3-Thiadiazolo[4,5-b]pyridines 174\u003c\/p\u003e \u003cp\u003e4.2.5 1,2,3-Thiadiazolo[4,5-c]pyridines 174\u003c\/p\u003e \u003cp\u003e4.2.6 1,2,3-Thiadiazolo[5,4-c]pyridines 176\u003c\/p\u003e \u003cp\u003e4.2.7 1,2,3-Thiadiazolo[5,4-d]pyrimidines 176\u003c\/p\u003e \u003cp\u003e4.2.8 1,2,3-Thiadiazolo[4,5-d]pyrimidines 178\u003c\/p\u003e \u003cp\u003e4.2.9 Pyrano[3,4-d][1,2,3]thiadiazole 179\u003c\/p\u003e \u003cp\u003e4.2.10 Thiopyrano[4,3-d][1,2,3]thiadiazoles 179\u003c\/p\u003e \u003cp\u003e4.2.11 Thiopyrano[2,1-d][1,2,3]thiadiazole 180\u003c\/p\u003e \u003cp\u003e4.2.12 Selenopyrano[4,3-d][1,2,3]thiadiazoles 181\u003c\/p\u003e \u003cp\u003e4.3 1,2,3-Thiadiazoles Fused with Seven-Membered Rings 181\u003c\/p\u003e \u003cp\u003e4.3.1 Benzooxepino- and Benzothiepino[3,4-d][1,2,3]thiadiazoles 181\u003c\/p\u003e \u003cp\u003e4.3.2 Thiadiazolo[5,4-d]benzazepines 182\u003c\/p\u003e \u003cp\u003e4.3.3 1,2,3-Thiadiazolo[5,4-b][1,5]benzodiazepine 182\u003c\/p\u003e \u003cp\u003e4.4 Bicyclic 1,2,3-Thiadiazoles of Azathiapentalenic Structure 183\u003c\/p\u003e \u003cp\u003eReferences 188\u003c\/p\u003e \u003cp\u003e\u003cb\u003e5 Synthesis and Properties of 1,2,3-Selenadiazoles 193\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e5.1 Synthesis of 1,2,3-Selenadiazoles 193\u003c\/p\u003e \u003cp\u003e5.1.1 Oxidative Cyclization of Hydrazones by Se-containing Reagents 193\u003c\/p\u003e \u003cp\u003e5.1.2 Cycloaddition Reactions of Diazoalkanes with Compounds Containing C=Se Bonds 197\u003c\/p\u003e \u003cp\u003e5.1.3 Elaboration of Preformed 1,2,3-Selenadiazoles 197\u003c\/p\u003e \u003cp\u003e5.1.4 Miscellaneous Syntheses 201\u003c\/p\u003e \u003cp\u003e5.2 Structural Data of 1,2,3-Selenadiazoles 201\u003c\/p\u003e \u003cp\u003e5.2.1 Mass Spectrometry 201\u003c\/p\u003e \u003cp\u003e5.2.2 Proton NMR Spectroscopy 201\u003c\/p\u003e \u003cp\u003e5.2.3 Carbon-13 NMR Spectroscopy 202\u003c\/p\u003e \u003cp\u003e5.2.4 Nitrogen-15 NMR Spectroscopy 202\u003c\/p\u003e \u003cp\u003e5.2.5 Selenium-77 NMR Spectroscopy 203\u003c\/p\u003e \u003cp\u003e5.2.6 X-ray Crystallography 203\u003c\/p\u003e \u003cp\u003e5.2.7 Miscellaneous 204\u003c\/p\u003e \u003cp\u003e5.3 Reactivity of 1,2,3-Selenadiazoles 204\u003c\/p\u003e \u003cp\u003e5.3.1 Ring Cleavage 204\u003c\/p\u003e \u003cp\u003e5.3.1.1 Thermal Reactions 204\u003c\/p\u003e \u003cp\u003e5.3.1.2 Photochemical Reactions 210\u003c\/p\u003e \u003cp\u003e5.3.1.3 Base-catalyzed Reactions 211\u003c\/p\u003e \u003cp\u003e5.3.1.4 Radical-catalyzed Reactions 214\u003c\/p\u003e \u003cp\u003e5.3.1.5 Reaction with Metal Complexes 215\u003c\/p\u003e \u003cp\u003e5.3.1.6 Miscellaneous Ring Cleavage Reactions 217\u003c\/p\u003e \u003cp\u003e5.3.2 Formation of Salts and Ylides 218\u003c\/p\u003e \u003cp\u003e5.4 Fused 1,2,3-Selenadiazoles 220\u003c\/p\u003e \u003cp\u003e5.4.1 Bicyclic 1,2,3-Selenadiazoles 220\u003c\/p\u003e \u003cp\u003e5.4.2 Tricyclic 1,2,3-Selenadiazoles 221\u003c\/p\u003e \u003cp\u003e5.4.3 Tetra- and Pentacyclic 1,2,3-Selenadiazoles 222\u003c\/p\u003e \u003cp\u003e5.5 Applications of 1,2,3-Selenadiazoles 222\u003c\/p\u003e \u003cp\u003eReferences 224\u003c\/p\u003e \u003cp\u003e\u003cb\u003e6 1,2,3-Thiadiazoles in Medicine and Agriculture 229\u003c\/b\u003e\u003c\/p\u003e \u003cp\u003e6.1 Medicine 229\u003c\/p\u003e \u003cp\u003e6.2 Agriculture 231\u003c\/p\u003e \u003cp\u003e6.2.1 Thidiazuron 232\u003c\/p\u003e \u003cp\u003e6.2.2 Bion 233\u003c\/p\u003e \u003cp\u003eReferences 236\u003c\/p\u003e \u003cp\u003eIndex 239\u003c\/p\u003e","brand":"John Wiley \u0026 Sons Inc","offers":[{"title":"Default Title","offer_id":49402564575575,"sku":"9780471326625","price":425.66,"currency_code":"GBP","in_stock":true}],"thumbnail_url":"\/\/cdn.shopify.com\/s\/files\/1\/0817\/1739\/5799\/files\/9780471326625.jpg?v=1730480774","url":"https:\/\/bookcurl.com\/products\/the-chemistry-of-123thiadiazoles-volume-62-9780471326625","provider":"Book Curl","version":"1.0","type":"link"}