1,4-Cycloaddition Reaction: The Diels-Alder Reaction in Heterocyclic Syntheses

1st Edition

The Diels-Alder Reaction in Heterocyclic Syntheses

Editors: Jan Hamer
Hardcover ISBN: 9780123957436
eBook ISBN: 9780323163118
Imprint: Academic Press
Published Date: 1st January 1967
Page Count: 512
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Organic Chemistry, Volume 8: 1,4-Cycloaddition Reactions: The Diels-Alder Reaction in Heterocyclic Syntheses describes 1,4-cycloaddition reactions leading to the formation of five- or six-membered heterocyclic compounds. Divided into 13 chapters, this book starts with an overview of various 1,4-cycloaddition reaction equations in the presence of at least one atom other than carbon. The following chapters describe the reaction mechanisms of five- or six-membered ring formed upon reaction with a dienophile, which contains an atom other than carbon. Considerable chapters are devoted to compounds used as dienophiles, including trivalent phosphorus, cyanogens and cyanogens-like compounds, imino, azo, carbonyl, thiocarbonyl, and diene compounds, as well as oxygen. Other chapters highlight some 1,4-cycloaddition reactions taking place through free radical intermediates.
This book is of value to organic and research chemists, as well as undergraduate and graduate organic chemistry students.

Table of Contents

List of Contributors Preface Chapter 1 Systems Capable of 1,4-Cycloaddition Reactions I. Introduction II. Five-membered Heterocyclic Systems III. Six-membered Heterocyclic Systems References Chapter 2 Formation of Five-membered Cyclic Sulfones I. Introduction II. Survey of the Conjugated Diene-Sulfur Dioxide Cycloaddition Reaction III. Thermal Dissociation of 2,5-Dihydrothiophene-1,1-dioxides IV. Related Cycloaddition Reactions References Chapter 3 Trivalent Phosphorus Compounds as Dienophiles I. Introduction II. Reaction of Phosphonous Dihalides with Dienes III. Reaction of Phosphorus Trihalides with Dienes IV. Reaction of Halophosphites with Dienes V. Related Diene-Phosphonous Dichloride Reactions VI. 1,4-Additions Involving Carbonyl Compounds Addendum References Chapter 4 Cyanogen and Cyanogen-like Compounds as Dienophiles I. Introduction II. Reaction Energetics III. Experimental Techniques and Results IV. Mechanism of Reaction V. Summarizing Tables References Chapter 5 Imino Compounds as Dienophiles I. Introduction II. Imines and Schiff Bases III. Immonium Salts IV. Imino Compounds of the —C(X)=NH Type V. Tables and Experimental Conditions References Chapter 6 Azo Compounds as Dienophiles I. Introduction II. Reactions with Acyclic Dienes III. Reactions with Cyclic Dienes IV. Reactions with Aromatic Compounds V. Reactions with Miscellaneous Compounds Appendix. Tabular Survey of the Diels-Alder Reaction Involving Azo Dienophiles References Chapter 7 Dienes Containing Two Nitrogen Atoms in the Conjugated System I. Introduction II. N=N—C=C Conjugated Systems III. N=C—N=C Conjugated Systems IV. C=N—N=C Conjugated Systems V. N=C—C=N Conjugated Systems VI. Heterocyclic Com


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© Academic Press 1967
Academic Press
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About the Editor

Jan Hamer