The Journal of Organic Chemistry

Nitroarylamines via the vicarious nucleophilic substitution of hydrogen: amination, alkylamination, and arylamination of nitroarenes with sulfenamides

M Ma̧kosza, M Bialecki

Index: Makosza, Mieczyslaw; Bialecki, Maciej Journal of Organic Chemistry, 1998 , vol. 63, # 15 p. 4878 - 4888

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Citation Number: 72

Abstract

A new reaction of sulfenamides with electrophilic arenes under basic conditions is described. The σ adducts formed from nitroarenes and the anions of sulfenamides undergo elimination of thiol to produce the corresponding o-and/or p-nitroanilines. This reaction is analogous to the known alkylation and hydroxylation of nitroarenes via the vicarious nucleophilic substitution of hydrogen (VNS). The reaction gives access to a wide range of ...