The Chemistry of Pyrroles

Organic Chemistry: A Series of Monographs, Vol. 34

1st Edition - January 1, 1977
Authors: R. Alan Jones, Gerritt P. Bean
Editors: Alfred T. Blomquist, Harry H. Wasserman
Language: English
eBook ISBN:
9 7 8 - 1 - 4 8 3 2 - 1 8 4 7 - 2

The Chemistry of Pyrroles, Volume 34 aims to provide a comprehensive survey of the synthesis of simple pyrroles and to present, wherever possible, a mechanistic and theoretical… Read more

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The Chemistry of Pyrroles, Volume 34 aims to provide a comprehensive survey of the synthesis of simple pyrroles and to present, wherever possible, a mechanistic and theoretical rationale for the multitude of reactions known for pyrroles. The book discusses the structure and reactivity of pyrrole; the synthesis of the pyrrole ring; and the electrophilic substitution of the pyrrole ring. The text also describes the oxidation and reduction of the pyrrole ring; the rearrangement and addition reactions; and the ketones, aldehydes, and carboxylic acid derivatives of pyrrole. Alkylpyrroles and related compounds; hydroxy- and aminopyrroles and related compounds; and azafulvenes are also considered. The book further tackles the physico-organic properties of pyrrole. Chemists and researchers of pyrrole chemistry will find the text invaluable.

ForewordAbbreviations and NomenclatureChapter 1. Introduction ReferencesChapter 2. The Structure and Reactivity of Pyrrole A. Molecular and Electronic Structure of Pyrrole B. Aromaticity and Resonance Energy C. Molecular Orbital Calculations on Pyrroles D. Theoretical Treatment of the Reactivity of Pyrrole with Electrophiles References Chapter 3. The Synthesis of the Pyrrole Ring A. Introduction B. 2+2 Carbon Units C. 1+3 Carbon Units D. From Four Carbon Units E. Ring-contractions F. Miscellaneous Reactions ReferencesChapter 4. Electrophilic Substitution of the Pyrrole Ring A. Introduction B. Protonation of the Pyrrole Ring C. Nitration and Nitrosation D. Halogenation E. C-Alkylation Reactions F. C-Acylation Reactions G. Reactions with Carbonyl Compounds H. Reactions of the Pyrryl Anion I. Miscellaneous Electrophilic Reactions J. Summary of the Reactivity of Pyrrole and Orientation Effects of Substituents References Chapter 5. Oxidation and Pyrrole Ring A. The Reactions of Pyrroles with Molecular Oxygen B. Oxidation by Chemical Reagents C. Anodic Oxidation of Pyrroles D. Reduction of the Pyrrole Ring ReferencesChapter 6. Rearrangement and Addition Reactions A. Thermal Rearrangements retaining the Pyrrole Ring B. Photochemical Rearrangements retaining the Pyrrole Ring C. Addition Reactions D. Reactions with Radicals ReferencesChapter 7. Ketones, Aldehydes and Carboxylic Acid Derivatives of Pyrrole A. Resonance Interaction between the Pyrrole Ring and the Carbonyl Substituent B. Chemical Reactivity References Chapter 8. Alkylpyrroles and Related Compounds A. Tautomerism B. Chemical Reactivity C. Silylpyrroles D. Pyrrolophanes and other Bridged Pyrroles ReferencesChapter 9. Hydroxy- and Aminopyrroles and Related Compounds A. Tautomerism B. Synthesis C. Chemical Reactivity D. Pyrrylthiols ReferencesChapter 10. Azafulvenes A. Structure and Reactivity B. Synthesis C. Spectroscopic Properties ReferencesChapter 11. Physico-Organic Properties of Pyrrole A. Molecular Association B. Basicity and Acidity Measurements C. Dipole Moments D. Polarographic Properties E. Electronic Spectra F. IR and Raman Spectra G. NMR Spectra H. Mass Spectra ReferencesIndex