Carbanion Chemistry

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This book was prepared with the idea of collecting some of the multitudinous new literature on carbanions and pre senting it along with the fundamentals of carbanion chemi stry. Some 400 papers from the period 1976 to 1982 have been assimilated into the book along with about an equal number of references (many to reviews) from the earlier literature. The material is organized under the headings Structures (with emphasis on the results of X-ray studies since they unambiguously show the molecular geometry), Preparations, and Reactions. Reactions, the largest topic, is divided into reactions with electrophiles, eliminations, oxidations, and rearrangements. Under these headings, carbanions without resonance stabilization (0' carbanions) are generally discus sed first, and are further subdivided into Sp3 (alkyl) followed by Sp2 (vinyl and aryl) followed by sp (acetylenic); resonance stabilized (n) hydrocarbon anions such as allyl and benzyl follow; lastly, heteroatom-containing n carbanions such as enolates are considered. Some references to carbanion equivalents are included at the end. Tucson, Arizona U.S.A. Robert B. Bates May 1983 Craig A. Ogle Table of Contents I. Introduction 1 II. Structures . 3 1. Non-delocalized (0") 3 a. Sp3 ..... . 3 b. Sp2 and sp . . . 7 2. Delocalized (n) . . 8 a. Hydrocarbon Anions 8 b. Heteroatom-containing Carbanions 10 III. Preparations. . . . . 13 13 1. From Alkyl Halides 13 a. With Metals . . 15 b. With Organometallics . 17 2. From Alkanes by Proton Abstraction 17 a. Acidities of CH Protons. . 21 b. Base-solvent Systems . . . 25 3. From Unsaturated Compounds 25 a. By Reduction . . . . . .

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From the review of the third edition:

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I. Introduction.- II. Structures.- 1. Non-delocalized (?).- 2. Delocalized (?).- III. Preparations.- 1. From Alkyl Halides.- 2. From Alkanes by Proton Abstraction.- 3. From Unsaturated Compounds.- 4. From Other Organometallics by Changing the Metal.- IV. Reactions of ? Carbanions with Electrophiles.- 1. Substitution Reactions of Alkyl, (sp3) Anions.- 2. Addition Reactions of Alkyl (sp3) Anions.- 3. Vinyl (sp2), Aryl (sp2), and Acetylenic (sp) Anions.- V. Reactions of ? Carbanions with Electrophiles.- 1. Hydrocarbon ? Anions.- 2. Enolate Anions.- 3. Other O-Stabilized Monoanions.- 4. O-Stabilized Dianions.- 5. N-stabilized Anions.- 6. S-stabilized Anions.- VI. Eliminations.- 1. ?-Eliminations.- 2. ?-Eliminations.- 3. ?-Eliminations.- 4. ?-Eliminations.- 5. Cycloeliminations.- VII. Oxidations.- 1. Oxidations to Hydroperoxides, Alcohols, and Ketones.- 2. Oxidative Couplings.- 3. Dianion Oxidations.- VIII. Rearrangements.- 1. Intermolecular Rearrangements.- 2. Intramolecular Additions.- 3.Intramolecular Eliminations.- 4. Sigmatropic Carbanion Rearrangements.- 5. Electrocyclic Carbanion Rearrangements.- 6. Complex Intramolecular Rearrangements.- IX. Carbanion Equivalents.- X. Summary.- XI. References.