Nucleophilic aromatic substitution in carbo- and heteroaromatic systems is a subject of considerable interest to chemists. This book uniquely addresses the systematic analysis of a vast range of nucleophilic substitutions of aromatic hydrogen.

Key Features

* This text provides coverage of: * Nucleophilic displacement of hydrogen (the S N/H reactions) in pi-deficient aromatics, such as nitroarenes, arene-metal complexes, and the like. * Nucleophilic displacement of hydrogen in heterocyclic substrates such as pyridines, their aza and benzo analogs, pyrylium and thiapyrylium cations, and other heterocycles * Mechanisms for the S N/H reactions (S N/H(AE), vicarious nucleophilic substitutions, and radical S N/H substitutions


Researchers in organic chemistry, pharmaceutical (industrial) chemistry, and materials chemistry; graduate and post-graduate students in organic synthesis.

Table of Contents

Introduction. Nucleophilic Substitution of Hydrogen in Arenes: Unactivated Arenes. Arene-Metal Complexes. Nitroarenes. Electrochemical S H/N [H over N] Reactions. Tropylium Salts and Other Non-Benzenoid Compounds. Intramolecular S H/N Reactions and Rearrangements Accompanied by S H/N Substitution. Nucleophilic Substitution of Hydrogen in Heteroaromatics: Azines. Azaaromatic Substrates Containing Quaternary Nitrogen. Pyrylium and Thiopyrylium Cations. Five-Membered Heterocycles. Electrochemical S H/N Reactions. Intramolecular S H/N Reactions in Heteroaromatics. Reactivity of Arenes and Hetarenes and Mechanisms of the S H/N Reactions: The Addition–Elimination S H/N(AW) Mechanism. The Elimination–Addition S H/N(EA) Mechanism. The S H/N(ANRORC) Mechanism. References. Subject Index.


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© 1994
Academic Press
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About the authors

Henk van der Plas

Professor Dr. H.C. van der Plas received his Ph.D. from the University of Amsterdam. He has served the Agricultural University at Wageningen, The Netherlands, from 1966 as a Reader, from 1970 as Professor of Organic Chemistry, and from 1978-1982 and 1989-1995 as Rector Magnificus. His research interest is in chemistry, mainly in the field of nucleophilic substitution and ring transformations. The results of his scientific results are set down in nearly 400 research papers, 20 review articles, and in two monographs, and a book (together with O. Chupakhin and V. Charushin), Nucleophilic Substitution of Aromatic Hydrogen.


@qu:"This is an excellent book that will prove useful for those interested in the chemistry of S<->N reactions." @source:--JOURNAL OF THE AMERICAN CHEMICAL SOCIETY