Azides and Nitrenes

Reactivity and Utility

1st Edition - September 11, 1984

Editor: Eric Scriven

eBook ISBN:

9 7 8 - 0 - 3 2 3 - 1 4 6 2 3 - 4

Azides and Nitrenes: Reactivity and Utility provides information pertinent to the fundamentals aspects of the chemistry of azides and nitrenes. This book discusses the mechanism… Read more

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Azides and Nitrenes: Reactivity and Utility provides information pertinent to the fundamentals aspects of the chemistry of azides and nitrenes. This book discusses the mechanism and synthetic applications of alkyl azides. Organized into 10 chapters, this book begins with an overview of the properties and chemistry of alkyl azides and alkylnitrenes. This text then examines the various pathways to the preparation of vinyl azides. Other chapters consider the magnetic resonance spectrum of phenyl azide, which may be taken as a representative to which more complex examples can be related. This book discusses as well the acyl azides and acylnitrenes that have their nitrogen function attached to electron-withdrawing groups not possessing a heteroatom bearing an unshared electron pair next to the nitrogen function. The final chapter deals with the main uses for organic azides involved in photochemical cross-linking of polymeric systems. This book is a valuable resource for chemists, spectroscopists, and theoreticians.

Contributors

Preface

1. Alkyl Azides and Nitrenes

I. Introduction

II. Physical Properties

III. Theoretical Aspects

IV. Preparation of Alkyl Azides

V. Mechanistic Aspects of the Decomposition of Alkyl Azides

VI. Synthetic Applications

References

2. Vinyl Azides and Nitrenes

I. Introduction

II. Synthesis of Vinyl Azides

III. Reactions of Vinyl Azides

IV. Vinylnitrenes

References

3. Aryl and Heteroaryl Azides and Nitrenes

I. Introduction

II. Preparative Methods

III. Reactions

References

4. Acyl Azides and Nitrenes

I. Introduction

II. Preparation of Acyl Azides

III. Spectra of Acyl Azides

IV. Cycloaddition Reactions of Acyl Azides

V. Nucleophilic Additions to the Azido Group of Acyl Azides

VI. Radical Reactions of Acyl Azides

VII. Acyl Azide Rearrangement with Loss of Nitrogen

VIII. Acylnitrenes

References

5. Azides and Nitrenes Attached to Elements Other than Carbon

I. Azides Attached to Elements Other than Carbon

II. Nitrenes Attached to Elements Other than Carbon

References

6. Nitrenium Ions

I. Introduction

II. Theoretical Calculations and Spectroscopy

III. Alkylnitrenium Ions

IV. Arylnitrenium Ions

V. Miscellaneous Nitrenium Ions

VI. Biological Properties

References

7. Physical and Spectroscopic Methods

I. Introduction

II. Nitrene and Simple Alkyl Derivatives

III. Aromatic Nitrenes

IV. Aminonitrenes

V. Nitrenium Ions

VI. Conclusions and Outlook

References

8. Gas-Phase and Matrix Studies

I. Introduction

II. Alkyl Azides and Nitrenes

III. Acyl, Thioacyl, and Carbamoyl Azides and Nitrenes

IV. Cyanogen Azide and Cyanonitrene

V. Aryl Azides and Nitrenes

VI. Phenylnitrene Radical-Cation

VII. Phenylnitrene Radical-Anion

References

9. Photoaffinity Labeling and Related Techniques

I. Introduction

II. Photochemistry of Aryl Azides

III. Photoaffinity Labeling

IV. Photochemical Cross-linking

V. Membrane Topography

VI. Aryl Azides Compared with Other Photochemical Reagents

VII. Future Directions

References

10. Industrial Applications

I. Photoresists and Printing Plates

II. Rubber Vulcanization

III. Cross-linking of Other Polymers

IV. Coupling Agents

V. Modification of Polymer Surfaces

VI. Tire-Cord Adhesives

VII. Dyes

VIII. Polymer Additives

IX. Blowing Agents and Gas Generators

X. Explosives and Propellants

XI. Biological Activity

XII. Polymerization Initiators

XIII. Miscellaneous Applications

References

Index