The Journal of Organic Chemistry

Hydroxylation of nitroarenes with alkylhydroperoxide anions via vicarious nucleophilic substitution of hydrogen

M Makosza, K Sienkiewicz

Index: Makosza, Mieczyslaw; Sienkiewicz, Krzysztof Journal of Organic Chemistry, 1990 , vol. 55, # 17 p. 4979 - 4981

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Citation Number: 44

Abstract

Summary: tert-Butyl and cumyl hydroperoxides in strongly basic media react with a variety of nitroarenes to produce 0- and/or p-nitrophenols. The reaction proceeds via an addition-base-induced 0-elimination pathway analogous to that of vicarious nucleophilic substitution. ... The replacement of hydrogen on aromatic rings with a variety of substituents via electrophilic aromatic substi- tution is one of the most important processes in organic ...