Electrochemical Reactions and Mechanisms in Organic Chemistry
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Table of contents
- Cover
- Contentsix
- Chapter 1. Electrochemical Oxidation and Reduction of Organic Compounds1
- General Technique1
- Anode arid Cathode Materials6
- Kinetics of Electron Transfer9
- Analytical arid Spectroscopic Techniques15
- Pulse Radiolysis22
- Chapter 2. Oxidation of Alkanes, Haloalkanes and Alkenes27
- Radical- Cations27
- Oxidation of Alkanes28
- Oxidation of Haloalkanes32
- Oxidation of Alkenes35
- Intramolecular Cyclization41
- Electrochemically Generated Reagents for Alketies45
- Chapter 3. Alkenes and Conjugated Alkenes, Reduction54
- Alkenes and Phenylalkenes54
- Alketie Radical-Anions as Nucleophiles56
- Activated Alketies – Introduction59
- Activated Alketies – Dimerization in Aprotic Media61
- Activated Alkenes – Dimerization in Protic Media64
- α,β-Unsaturated Aldehydes and Ketones69
- Intramolecular Cyclization74
- Mixed Hydrocoupling Reactions80
- Asymmetric Reduction80
- Electrocatalytic Hydrogenation83
- Chapter 4. Reductive Bond Cleavage Processes - I89
- Dissociative Electron Transfer89
- Reduction of Alkyl and Benzyl Halides98
- Reactions of the Trichloromethyl Group106
- Reductive Cyclization of α, ω-Dihaloalkanes110
- Alketies from 1,2-Dibromides and Related Compounds115
- Reduction of Aryl Halides122
- Electrochemically Induced SRNl Reaction126
- Electrochemically Induced Radical Cyclization Reactions of Aryl Halides128
- Carbon-Halogen Bond Reactions Catalysed by the Anode Material134
- Carbon-Halogen Bond Reactions Catalysed by Ni, Co and Pd Complexes137
- Reactions with Carbon Dioxide147
- Chapter 5. Reductive Bond Cleavage Processes - II158
- Introduction158
- Carbotn-Oxygen Bond Cleavage160
- Quaternary Ammonium Salts164
- Quaternary Phosphonium and Arsonuim Salts166
- Carbon-Sulphur and Related Bond Cleavage168
- Cleavage Assisted by an adjacent Carbonyl Function175
- Carbon-Carbon Bond Cleavage180
- The Abnormal Clemmensen Reaction181
- Chapter 6. Oxidation of Aromatic Rings187
- Radical-Cations187
- Oxidative Substitution Reactions192
- Oxidation of Phenols203
- Intramolecular Cyclization Processes211
- Oxidation of Anilines218
- Oxidation of Aromatic Heterocycles222
- Chapter 7. Reduction of Aromatic Rings239
- Aromatic compounds Radical-Anions239
- Aromatic Hydrocarbon243
- Thiophene, Pyrrole and Indole Derivatives247
- Pyridine, Quinolne and Isoquinoline Derivatives248
- Other Nitrogen Heterocycles252
- Nitrogen-Nitrogen Bond cleavage254
- Reductive Alkylation and Carboxylation255
- Electrocatalytic Hydrogenation256
- Chapter 8. Alcohols, Amines and Amides, Oxidation261
- Nitroxyl Radicals261
- Oxidation of Alcohols261
- Oxidation of Amides and Sulphonamides276
- Oxidation of Amides and Urethanes282
- Oxidation of Hydrazine Derivatives290
- Chapter 9. Aldehydes, Ketones and Carboxylic Acids, Oxidation300
- Oxidation of Ketones300
- Oxidation of Aldehydes303
- Oxidation of Etiolate Ions305
- Oxidation of Hydrazones and Oximes308
- Oxiddon of Carboxylate – Introduction and Mechanism312
- The Kolbe Reaction316
- The Non- Kolbe Reaction322
- Chapter 10. Reduction of Carbonyl Compounds and their Derivatives330
- Carbonyl Compounds Radical-anions330
- Aromatic Carbonyl Compounds - Mechanistic Studies332
- Aromatic Carbonyl Compounds - Enantiomeric Reduction336
- Aromatic Carbonyl Compounds - Carboxylation Reaction339
- Aliphatic Carbonyl Compounds340
- The Electrochemical Clemmensen Reaction344
- Coupling with Unsaturated Functions344
- Reduction of Dicarbonly Compounds350
- Reduction of β- Ketoesters - The Tafel Rearrangement351
- Carboxlic Acid Reduction352
- Esters and Lactones354
- Acid Amides355
- Acid Chlorides357
- Imines, Oximes and Hydrazones359
- Electrocatalytic Hydrogenation364
- Chapter 11 . Reduction of Nitro, Nitroso, Azo and Azoxy Groups371
- Nitro- and Nitroso-compounds Radical-Anions371
- Aliphatic Nitrocompounds373
- Formation of Arylamines376
- Formation of Nitrosoarenrs and Arylhydroxylamines379
- Rearrangement of Phenylhydroxylamines - Formation of 4-Aminophenols381
- Formation of Heterocyclic Rings383
- Azoxybenzenes, Azobenzenes and Hydrazobenzenes387
- Nitramines and Nitrosamines390
- Benzenediazonium Salts392
Electrochemical reactions make significant contributions to organic synthesis either in the laboratory or on an industrial scale. These methods have the potential for developing more "green" chemical synthesis. Over recent years, modern investigations have clarified the mechanisms of important organic electrochemical reactions. Progress has also been made in controlling the reactivity of intermediates through either radical or ionic pathways. Now is the time to gather all the electrochemical work into a textbook.
As an essential addition to the armory of synthetic organic chemists, electrochemical reactions give results not easily achieved by many other chemical routes. This book presents a logical development of reactions and mechanisms in organic electrochemistry at a level suited to research scientists and final year graduate students. It forms an excellent starting point from which synthetic organic chemists, in both academia and industry, can appreciate uses for electrochemical methods in their own work. The book is also a reference guide to the literature.