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

The Diels-Alder Reaction in Heterocyclic Syntheses

1st Edition - January 1, 1967

Editor: Jan Hamer

eBook ISBN:

9 7 8 - 0 - 3 2 3 - 1 6 3 1 1 - 8

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… Read more

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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.

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 Compounds

VII. Experimental Procedures

References

Chapter 8 Carbonyl and Thiocarbonyl Compounds as Dienophiles

I. Scope and Introduction

II. Carbonyl Compounds as Dienophiles

III. Thiocarbonyl Compounds as Dienophiles

Appendix

References

Chapter 9 α,ß-Unsaturated Carbonyl Compounds as Dienes

I. Dimerization Reactions

II. α,ß-Unsaturated Carbonyl Compounds as Dienes

Conclusions

References

Chapter 10 Oxygen as a Dienophile

I. General Aspects

II. Photosensitized Cycloaddition of Oxygen to Conjugated Diene Systems

III. Photochemical Cycloaddition of Oxygen to Aromatic Compounds

IV. Photochemical Cycloaddition of Oxygen to Aryl-substituted Carbo- and Heterocyclic Pentadienes

Appendix. Tabular Survey of Adducts of Aromatic Hydrocarbons

References

Chapter 11 Cycloadditions to o-Quinones, 1,2-Diketones, and Some of Their Derivatives

I. General Survey

II. Formation of 2,3-Dihydro-l,4-dioxins ("1,4-Dioxenes")

III. Formation of 1,3,2-Dioxathioles

IV. Formation of 1,3,2-Dioxaphospholes

V. Formation of 1,3-Dioxoles

VI. Formation of Oxazoles

VII. Formation of 1,4,5-Oxadiazepines

References

Chapter 12 Nitroso Compounds as Dienophiles

I. Introduction

II. The Formation of Oxazine Derivatives

III. Structure Proof of the Cycloaddition Products

IV. The Direction of the Cycloaddition Reaction

V. The Kinetics of the Cycloaddition Reaction

VI. Properties and Synthetic Use of the Cycloadducts

VII. Experimental Procedures

References

Chapter 13 N-Sulfinyl Compounds as Dienophiles

I. Introduction and Scope

II. 1,4-Cycloaddition Reactions of N-Sulfinyl Compounds

III. Orientation in the 1,4-Cycloaddition Reaction

IV. Properties of the Cycloadducts

V. Reactions of the Cycloadducts

VI. Experimental Procedures

References

Addendum

Author Index

Subject Index