Pyrolytic Methods in Organic Chemistry - 1st Edition - ISBN: 9780121380502, 9780323154178

Pyrolytic Methods in Organic Chemistry

1st Edition

Application of Flow and Flash Vacuum Pyrolytic Techniques

Authors: Roger Brown
eBook ISBN: 9780323154178
Imprint: Academic Press
Published Date: 28th April 1980
Page Count: 362
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Pyrolytic Methods in Organic Chemistry: Application of Flow and Flash Vacuum Pyrolytic Techniques is concerned with the use of flow pyrolysis and flash vacuum pyrolysis in preparative organic chemistry. Topics covered include pyrolytic generation and reactions of free radicals, arynes, and cyclobutadienes; elimination reactions; rearrangements of carbenes and nitrenes in the gas phase; and fragmentation of cyclic and acyclic structures. Examples of the types of reaction for which flow and flash pyrolytic methods are well suited are provided.
This book is comprised of nine chapters and begins by discussing the place of flow and flash vacuum pyrolytic methods in organic chemistry. The next chapter gives an account of apparatus and experimental methods, while the remaining chapters focus on pyrolytic reactions that are grouped together according to the nature of the overall process, the formal structure of the starting material, and mechanistic type. Reactions that are formally related because they involve elimination of a small fragment molecule X-X or X-Y from a larger molecular framework are examined, along with cleavage of carbocyclic systems. The final chapter presents examples of high-temperature rearrangements, focusing on electrocyclic reactions and cycloadditions involving mainly four or six electrons; reactions that proceed through diradical intermediates; and isomerizations of heterocyclic rings. This monograph is intended mainly for practicing academic and industrial organic chemists and for advanced and graduate students.

Table of Contents


Terminology and Conventions

Chapter 1. The Place of Flow and Flash Vacuum Pyrolytic Methods in Organic Chemistry

I. Historical Introduction

II. Scope of This Book and of Previous Reviews

III. Scope of Pyrolytic Experiments

IV. Thermal, Photochemical, and Mass Spectral Processes and Their Correlation


Chapter 2. Apparatus and Methods

I. Introduction

II. Apparatus

III. Choice of Pyrolytic Conditions


Chapter 3. Pyrolytic Generation and Reactions of Free Radicals, Arynes, and Cyclobutadienes

I. Introduction

II. Physical Detection, Identification, and Spectroscopic Study of Free Radicals

III. Pyrolytic Generation of Some O-, S-, and N-Centered Radicals

IV. Pyrolytic Formation of Carbon Radicals from Relatively Stable Precursors

V. Trapping of Arynes Formed at High Temperatures

VI. Pyrolytic Generation of Cyclobutadiene and Benzocyclobutadiene


Chapter 4. Elimination Reactions

I. Introduction

II. Dehydrogenations and Dealkylations

III. α-Eliminations

IV. β-Eliminations and γ-Eliminations

V. Formation of Ketenes by β-Elimination

VI. 1,4-Eliminations of HX from Systems H — C = C = C — X


Chapter 5. Generation of Carbenes and Nitrenes and Their Rearrangements in the Gas Phase

I. Introduction

II. Formation and Rearrangement of Carbenes

III. Rearrangements Involving Aromatic Carbenes and Nitrenes

IV. Sulfonylnitrenes and Carbamoylnitrenes


Chapter 6. Fragmentation of Cyclic Structures with Elimination of Small Molecules

I. Introduction

II. Pyrolysis of Carbonyl Compounds and Some Related Thionyl and Sulfonyl Compounds

III. Pyrolysis of Cyclic Sulfoxides and Sulfones

IV. Fragmentation of Various Heterocyclic and Polyheterocyclic Compounds


Chapter 7. Fragmentation of Acyclic Structures, and Related Cleavage of Cyclic Structures

I. Decarboxylations and Decarbonylations

II. Fission and Ring Opening of γ ,δ-Unsaturated Alcohols

III. Retro-Ene Reactions


Chapter 8. Cleavage of Carbocyclic Systems with Related Heterocyclic Examples

I. Introduction

II. Cleavage of Cyclobutane Derivatives

III. Retro-Diels-Alder Reactions

IV. Miscellaneous Fragmentations


Chapter 9. Rearrangements without Fragmentation

I. Introduction

II. Rearrangements with Concerted Four- or Six-Electron Steps

III. Rearrangements with Diradical or Dipolar Intermediates

IV. Concerted Rearrangements of Cyclopropane Derivatives

V. Sigmatropic Rearrangements

VI. Miscellaneous Isomerizations of Heterocyclic Compounds

VII. Rearrangements with Migration of a Coordinated Metal Atom




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© Academic Press 1980
Academic Press
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About the Author

Roger Brown

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