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Reactions of Organosulfur Compounds - 1st Edition - ISBN: 9780121070502, 9781483216430

Reactions of Organosulfur Compounds

1st Edition

Organic Chemistry: A Series of Monographs, Vol. 37

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Author: Eric Block
Editors: Alfred T. Blomquist Harry H. Wasserman
eBook ISBN: 9781483216430
Imprint: Academic Press
Published Date: 1st January 1978
Page Count: 336
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Organic Chemistry, Volume 37: Reactions of Organosulfur Compounds covers the basics of organosulfur chemistry and the characteristics of organically bound sulfur, with an emphasis on reactions, particularly those of synthetic utility. The book discusses the preparation, nature, stereochemical aspects, reactions, and the kinetic and thermodynamic assessment of the stability of sulfur-containing carbanions; the preparation and reactions of sulfur ylides; and the preparation, assessment of stability, and reactions of sulfur-containing carbocations. The text also describes preparation, assessment of stability, nature, and reactions of sulfur-containing radicals, organosulfur carbenes, and carbenoids; as well as the the pericyclic reactions of organosulfur compounds. Chemists, biochemists, and students taking related courses will find the book useful.

Table of Contents

List of Tables




1 Introduction

1.1 Prologue

1.2 A Word on Odor

1.3 Sulfur in the Natural Environment

1.4 Nomenclature and Synthesis of Organosulfur Compounds

1.5 3d Orbital Effects

1.6 Other Bonding Properties of Sulfur

1.7 Spectroscopic Properties of Sulfur

1.8 Penicillin and Cephalosporin Chemistry: A Microcosm of Organosulfur Chemistry


2 Sulfur-Containing Carbanions

2.1 Introduction

2.2 Preparation

2.3 Kinetic and Thermodynamic Assessment of Stability of Sulfur-Containing Carbanions

2.4 The Nature of Carbanion Stabilization by Sulfur

2.5 Stereochemical Aspects of α-Sulfonyl Carbanions

2.6 Stereochemical Aspects of α-Sulfìnyl Carbanions

2.7 Reactions of Sulfur-Containing Carbanions


3 Sulfur Ylides

3.1 Preparation

3.2 σ- and π-Sulfuranes

3.3 Thiabenzenes 96

3.4 Thiocarbonyl Ylides (Thione Ylides)

3.5 Reactions of Sulfur Ylides


4 Sulfur-Containing Carbocations

4.1 Introduction

4.2 Generation of Sulfur-Containing Carbocations

4.3 Assessment of Stability of Sulfur-Containing Carbocations

4.4 Neighboring Group Participation by Divalent Sulfur

4.5 Reactions of Thiocarbocations

4.6 The Pummerer Rearrangement

4.7 Beckmann Fragmentation of α-Alkylthioketoximes

4.8 Carbocations Containing the Sulfinyl and Sulfonyl Groups

4.9 Carbocations Containing the Disulfide Group


5 Sulfur-Containing Radicals

5.1 Introduction

5.2 Generation and Reactions of Sulfur-Containing Radicals

5.3 Kinetic Assessment of Stability of Sulfur-Substituted Radicals

5.4 The Study of Sulfur-Containing Radicals by Electron Spin Resonance Spectroscopy

5.5 The Nature of Radical Stabilization by Sulfur

5.6 α-Disulfìde Radicals

5.7 α-Sulfìnyl Radicals

5.8 α-Sulfonyl Radicals

5.9 The Dibenzenesulfenamidyl Radical

5.10 The Stevens Rearrangement

5.11 The Wittig Rearrangement

5.12 Sulfur-Centered Radicals


6 Organosulfur Carbenes and Carbenoids

6.1 Introduction

6.2 Generation

6.3 Reactions of α-Thiomethylenes: Cycloaddition to Multiple Bonds

6.4 Other Reactions of α-Thiomethylenes: General Survey

6.5 Reactions of ß-, γ-, and δ-Thiomethylenes

6.6 Sulfinyl- and Sulfonylmethylenes


7 Pericyclic Reactions of Organosulfur Compounds

7.1 Introduction

7.2 Sigmatropic Rearrangements

7.3 Electrocyclic Processes

7.4 Cycloaddition Reactions

7.5 Cycloelimination Reactions


Appendix A Bibliography of Recent Books on Sulfur

Appendix B Additional Tables



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© Academic Press 1978
1st January 1978
Academic Press
eBook ISBN:

About the Author

Eric Block

About the Editors

Alfred T. Blomquist

Harry H. Wasserman

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