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Homolytic Aromatic Substitution - 1st Edition - ISBN: 9780080092461, 9781483151137

Homolytic Aromatic Substitution

1st Edition

International Series of Monographs on Organic Chemistry

Author: G. H. Williams
Editors: D. H. R. Barton W. Doering
eBook ISBN: 9781483151137
Imprint: Pergamon
Published Date: 1st January 1960
Page Count: 142
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Homolytic Aromatic Substitution deals with the theoretical aspects of homolytic aromatic substitution reactions. The effect of various kinds of free radicals on the substitution of atoms or groups (usually hydrogen) attached to aromatic nuclei is examined, and the preparative use of homolytic substitution reactions is also considered. This book is comprised of seven chapters and begins with an introduction to the general characteristics of homolysis, along with homolytic and heterolytic aromatic substitution. The discussion then turns to the various theoretical approaches used to rationalize aromatic substitution, particularly those that are germane to a consideration of the problems of orientation and reactivity in homolytic substitution. The following chapters explore homolytic arylation reactions, including those between aryl radicals and aromatic substrates; relative rates of arylation and partial rate factors for phenylation; the reaction mechanism underlying intramolecular arylation; and homolytic alkylation reactions. The final chapter deals with hydroxylation and some other substitution reactions such as benzoyloxylation, acetyloxylation, halogenation, amination and amidation, and mercuration. This monograph will be of interest to organic chemists.

Table of Contents


1. General Introduction

1 General Characteristics of Homolytic Reactions

2 Homolytic and Heterolytic Aromatic Substitution

2. Theoretical Treatments of Aromatic Substitution

1 Introduction

2 General Assumptions of the Isolated Molecule and Transition State Methods

3 Isolated Molecule (I.M.) Approach

4 Transition State (T.S.) Approach

5 Influence of the Reagent

6 General Discussion

3. Homolytic Arylation Reactions

1 Introduction

2 Arylation with Diazo and Azo Compounds

3 Arylation with Diacyl Peroxides and Analogous Substances

4 Arylation with Aryl Radicals Obtained by Photolysis

4. Quantitative Investigation of Homolytic Arylation

1 Reaction Mechanism

2 Relative Rates of Arylation

3 Ratios of Isomers

4 Partial Rate Factors for Phenylation

5. Intramolecular Arylation

1 Introduction

2 Experimental Methods

3 Reaction Mechanism

6. Alkylation

1 Homolytic Alkylation Reactions

2 Quantitative Study of Homolytic Alkylation

7. Hydroxylation and Some Other Substitution Reactions

1 Hydroxylation

2 Benzoyloxylation

3 Acetyloxylation

4 Halogenation

5 Amination and Amidation

6 Mercuration

Author Index

Subject Index


No. of pages:
© Pergamon 1960
1st January 1960
eBook ISBN:

About the Author

G. H. Williams

About the Editors

D. H. R. Barton

W. Doering

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