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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.
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
III. Choice of Pyrolytic Conditions
Chapter 3. Pyrolytic Generation and Reactions of Free Radicals, Arynes, and Cyclobutadienes
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
II. Dehydrogenations and Dealkylations
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
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
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
II. Cleavage of Cyclobutane Derivatives
III. Retro-Diels-Alder Reactions
IV. Miscellaneous Fragmentations
Chapter 9. Rearrangements without Fragmentation
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
- No. of pages:
- © Academic Press 1980
- 28th April 1980
- Academic Press
- eBook ISBN:
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