COVID-19 Update: We are currently shipping orders daily. However, due to transit disruptions in some geographies, deliveries may be delayed. To provide all customers with timely access to content, we are offering 50% off Science and Technology Print & eBook bundle options. Terms & conditions.
The Chemistry of Pyrroles - 1st Edition - ISBN: 9780123898401, 9781483218472

The Chemistry of Pyrroles

1st Edition

Organic Chemistry: A Series of Monographs, Vol. 34

Authors: R. Alan Jones Gerritt P. Bean
Editors: Alfred T. Blomquist Harry H. Wasserman
eBook ISBN: 9781483218472
Imprint: Academic Press
Published Date: 1st January 1977
Page Count: 538
Sales tax will be calculated at check-out Price includes VAT/GST
Price includes VAT/GST

Institutional Subscription

Secure Checkout

Personal information is secured with SSL technology.

Free Shipping

Free global shipping
No minimum order.


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.

Table of Contents


Abbreviations and Nomenclature

Chapter 1. Introduction


Chapter 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


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


Chapter 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


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


Chapter 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


Chapter 7. Ketones, Aldehydes and Carboxylic Acid Derivatives of Pyrrole

A. Resonance Interaction between the Pyrrole Ring and the Carbonyl Substituent

B. Chemical Reactivity


Chapter 8. Alkylpyrroles and Related Compounds

A. Tautomerism

B. Chemical Reactivity

C. Silylpyrroles

D. Pyrrolophanes and other Bridged Pyrroles


Chapter 9. Hydroxy- and Aminopyrroles and Related Compounds

A. Tautomerism

B. Synthesis

C. Chemical Reactivity

D. Pyrrylthiols


Chapter 10. Azafulvenes

A. Structure and Reactivity

B. Synthesis

C. Spectroscopic Properties


Chapter 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




No. of pages:
© Academic Press 1977
1st January 1977
Academic Press
eBook ISBN:

About the Authors

R. Alan Jones

Gerritt P. Bean

About the Editors

Alfred T. Blomquist

Harry H. Wasserman

Ratings and Reviews