Fundamentals of Carbanion Chemistry - 1st Edition - ISBN: 9780123957603, 9780323162449

Fundamentals of Carbanion Chemistry

1st Edition

Authors: Donald J. Cram
eBook ISBN: 9780323162449
Imprint: Academic Press
Published Date: 1st January 1965
Page Count: 298
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Organic Chemistry, Volume 4: Fundamentals of Carbanion Chemistry provides information pertinent to carbanion chemistry. This book explores several topics, including carbonium ions, carbanions, carbenes, and carbon radicals. Comprised of six chapters, this volume starts with an overview of the variation of the kinetic and thermodynamic acidities of carbon acids with substituents and environments. This text then explores the methods of carbanion stabilization by substituents and discusses the various types of stabilization. Other chapters explain the stereochemistry of hydrogen–deuterium exchange and examine the stereochemistry of substitution reactions of organometallic compounds. This book discusses as well the structure and immediate environment of reaction intermediates through the use of stereochemical techniques. The final chapter considers the unsaturated anionic rearrangements of carbanions, carbonium ions, as well as carbon radicals and other rearrangements. Chemists, organic chemists, researchers, and graduate students interested in the field of carbanion chemistry will find this book extremely useful.

Table of Contents


Chapter I Carbon Acids

Thermodynamic Acidity Scales

Correlations between Thermodynamic and Kinetic Acidity

Kinetic Acidities of Weak Hydrocarbon Acids

Effect of Medium on Kinetic and Equilibrium Acidity of Carbon Acids

Chapter II Carbanion Structure and Mechanism of Stabilization

s-Character Effects

Conjugative Effects

Inductive Effects

Homoconjugative Effects

Aromatization Effects

Negative Hyperconjugative Effects

d-Orbital Effects

Chapter III Stereochemistry of Substitution of Carbon Acids and Organometallic Compounds

Carbon Acids That Form Symmetrical or near Symmetrical Carbanions

Systems That Form Unsymmetrical Carbanions

Special Case of Carbanions Confined in Three-Membered Rings

Homoconjugated Carbanions

Stereochemistry of Substitution of Organometallic Compounds

Chapter IV Stereochemistry of Carbanions Generated with Different Leaving Groups

Carbon as Leaving Group in Electrophilic Substitution at Saturated Carbon

Other Leaving Groups in Electrophilic Substitution at Saturated Carbon

Comparison of the Stereochemical Capabilities of Carbanions and Carbonium Ions

Chapter V Isomerization by Proton Transfer in Unsaturated Systems


Geometric Stability of Allylic Anions

Hydrocarbon Substituent Effects on the Rates of Allylic Rearrangements of Alkenes

Olefin Equilibria

Collapse Ratios for Allylic Anions

Chapter VI Molecular Rearrangements

Ring-Chain Anionic Rearrangements


Rearrangements with 1,3-Elimination Reaction Stages

Author Index

Subject Index


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© Academic Press 1965
Academic Press
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About the Author

Donald J. Cram

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