Organic Reaction Mechanisms 2010 -- Contents -- Chapter 1. Reactions of Aldehydes and Ketones and their Derivatives -- Formation and Reactions of Acetals and Related Species -- Reactions of Glucosides -- Reactions of Ketenes -- Formation and Reactions of Nitrogen Derivatives -- Synthesis of Imines -- The Mannich Reaction -- Addition of Organometallics -- Other Arylations, Alkenylations, and Allylations of Imines -- Reduction of Imines -- Iminium Species -- Other Reactions of Imines -- Oximes, Hydrazones, and Related Species -- C−C Bond Formation and Fission: Aldol and Related Reactions -- Reviews of Organocatalysts -- Asymmetric Aldols Catalysed by Proline and its Derivatives -- Other Asymmetric Aldols -- Mukaiyama and Vinylogous Aldols -- Other Aldol and Aldol-type Reactions -- The Henry (Nitroaldol) Reaction -- The Baylis-Hillman Reaction and its Morita-variant -- Allylation and Related Reactions -- The Horner-Wadsworth-Emmons Reaction and Other Olefinations -- Alkynylations -- Benzoin Condensation and Pinacol Coupling -- Michael Additions -- Miscellaneous Condensations -- Other Addition Reactions -- Addition of Organozincs -- Arylations -- Addition of Other Organometallics, Including Grignards -- The Wittig Reaction -- Hydrocyanation, Cyanosilylation, and Related Additions -- Hydrosilylation, Hydrophosphonylation, and Related Reactions -- Enolization and Related Reactions -- α-Halogenation, α-Alkylation, and Other α-Substitutions -- Oxidation and Reduction of Carbonyl Compounds -- Regio-, Enantio-, and Diastereo-selective Reduction Reactions -- Other Reduction Reactions -- Oxidation Reactions -- Atmospheric Reactions -- Other Reactions -- References -- Chapter 2. Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and their Derivatives -- Intermolecular Catalysis and Reactions -- Carboxylic Acids and their Derivatives -- (a) Acids.

(b) Esters -- (c) Acyl Halides -- (d) Amides and Imides -- (e) Carbonates, Carbamates, and Hydrazides -- (f) Other Heterocyclic Nitrogen Centres -- (g) Thioesters, Thiocarbonates, Thiocarbamates, and Thioacyl Halides -- Phosphoric Acids and their Derivatives -- (a) Phosphoryl and Phosphonyl Halides -- (b) Thiophosphates and Thiophosphonates -- Sulfonic Acids and their Derivatives -- (a) Sulfonates -- Intramolecular Catalysis and Neighbouring Group Participation -- Association-Prefaced Catalysis -- Biologically Significant Reactions -- Carboxylic Acids and their Derivatives -- (a) Acids -- (b) Esters and Carbonates -- (c) Amides -- Phosphoric Acids and their Derivatives -- (a) Phosphate and Phosphonate Monoesters -- (b) Phosphate and Phosphonate Diesters -- (c) Phosphate Triesters -- (d) Phosphoramidates -- References -- Chapter 3. Oxidation and Reduction -- Oxidation by Metal Ions and Related Species -- Chromium, Manganese, and Nickel -- Copper, Silver, Gold, and Thallium -- Cerium and Vanadium -- Bismuth and Palladium -- Group VIII Metals -- Oxidation by Compounds of Non-metallic Elements -- Nitrogen and Sulfur -- Halogens -- Ozonolysis and Ozonation -- Peracids and Peroxides -- Photo-oxygenation and Singlet Oxygen -- Triplet Oxygen and Autoxidation -- Other Oxidations -- Reduction by Complex Metal Hydrides -- Hydrogenation -- Transfer Hydrogenation -- Other Reductions -- References -- Chapter 4. Carbenes and Nitrenes -- Reviews -- Generation, Structure, and Reactivity -- Carbenes in Coordination Chemistry -- Addition - Fragmentations -- Free Carbenes or Main Group Carbenoids Reactions -- Transition-metal-assisted Reactions -- Insertion - Abstraction -- Free Carbenes or Carbenoids Reactions -- Transition-metal-assisted Reactions -- Rearrangements -- Free Carbenes or Carbenoids Reactions -- Nucleophilic Carbenes - Carbenes as Organocatalysts.

Nitrenes -- Heavy-atom Carbene Analogues -- References -- Chapter 5. Nucleophilic Aromatic Substitution -- General -- The SNAr Mechanism -- Heterocyclic Systems -- Meisenheimer and Related Complexes -- References -- Chapter 6. Electrophilic Aromatic Substitution -- General -- Halogenation -- Nitration -- Alkylation, Acylation, and Arylation Reactions -- Substitutions on Heterocyclic Rings -- Other Reactions -- References -- Chapter 7. Carbocations -- Introduction -- Alkyl and Cycloalkyl Carbenium Ions -- Benzyl Cations and Quinone Methides -- Benzhydryl, Trityl, and Fluorenyl Cations -- Carbocation Reactivity - Quantitative Studies -- Oxygen- and Sulfur-stabilized Cations -- Carbocations Containing Silicon and Other Group 14 Elements -- Halogenated Carbocations -- Allyl and Vinyl Cations -- Aryl Cations -- Arenium Ions -- Nitrenium Ions -- Aromatic Systems -- Dications -- Polycyclic Systems -- Carbonium (Bridged) Ions -- Carbocations in Biosynthesis -- References -- Chapter 8. Nucleophilic Aliphatic Substitution -- Allylic and Vinylic Substitutions -- Reactions of Cyclic Ethers -- Aziridines and Other Small Ring Substitutions -- Studies Using Kinetic Isotope Effects -- Nucleophilic Substitution on Elements Other than Carbon -- Medium Effects/Solvent Effects -- Micelles and Ion Pair Aggregates in Substitution Reactions -- Structural Effects -- Theoretical Studies -- Gas-phase Substitution Reactions -- Miscellaneous Kinetic and Product Studies -- Acknowledgement -- References -- Chapter 9. Carbanions and Electrophilic Aliphatic Substitution -- Carbanion Structure and Stability -- Carbanion Reactions -- Enolates and Related Species -- Heteroatom-stabilized Species -- Organometallic Species -- Proton-transfer Reactions -- Miscellaneous -- Electrophilic Aliphatic Substitution -- References -- Chapter 10. Elimination Reactions -- E1cB and E2 Mechanisms.

Pyrolytic Reactions -- Acid Derivatives -- Halogen Derivatives -- Oxygen Derivatives -- Nitrogen Derivatives -- Other Pyrolytic Reactions -- Elimination Reactions in Synthesis -- Other Reactions -- References -- Chapter 11. Addition Reactions: Polar Addition -- Reviews -- Electrophilic Additions -- Halogenation and Related Reactions -- Additions of ArSX, ArSeX, and Related Reagents with Electrophilic Sulfur -- Additions of Hydrogen Halides and Other Brønsted Acids -- Additions of Electrophilic Carbon -- Additions of Electrophilic Nitrogen -- Additions Initiated by Metals and Metal Ions as Electrophiles -- Miscellaneous Electrophilic Additions -- Nucleophilic Additions -- Additions to Multiple Bonds Conjugated with C=O -- Additions to Multiple Bonds Activated by Other Electron-withdrawing Groups -- Additions of Organometallics to Activated Double Bonds -- Miscellaneous Nucleophilic Additions -- References -- Chapter 12. Addition Reactions: Cycloaddition -- 2 + 2-Cycloaddition -- 2 + 3-Cycloaddition -- 2 + 4-Cycloaddition -- Miscellaneous Cycloadditions -- References -- Chapter 13. Molecular Rearrangements: Part 1. Pericyclic Reactions -- [3,3]-Sigmatropic, Claisen, and Cope Rearrangements -- [2,3]-Reactions -- Vinyl Cyclobutane and Vinyl Cyclopropane Rearrangement -- 1,2-Migration -- Ene Reaction -- Bergman Reaction -- Electrocyclic Reactions -- Cyclization -- 4 + 2-Cycloadditions -- 3 + 2-Cycloadditions -- Metathesis -- Metal-catalysed Reactions -- Miscellaneous -- References -- Chapter 14. Molecular Rearrangements: Part 2. Other Reactions -- Aromatic Rearrangement -- Ionic Rearrangements -- Anionic Rearrangements -- Cationic Rearrangements -- Rearrangements Involving Electron-deficient Heteroatoms -- Rearrangements Catalysed by Metals -- Organo-catalysed Rearrangements -- Rearrangements Involving Ring Opening -- Isomerizations -- Tautomerism.

Radical Rearrangements -- References -- Author Index -- Subject Index.