Tetrahedron

Unusual reaction of 1, 4-diamino-2-nitrobenzene derivatives toward nucleophiles: Catalysis by sodium sulphite

L Forlani, C Boga, M Mazza, V Cavrini, V Andrisano

Index: Forlani, Luciano; Boga, Carla; Mazza, Milena; Cavrini, Vanni; Andrisano, Vincenza Tetrahedron, 1998 , vol. 54, # 18 p. 4647 - 4654

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Citation Number: 6

Abstract

Unusual substitution of amino group occurs by reactions of some 1, 4-diamino-2- nitrobenzenes (semipermanent hair dyes) and nucleophiles (NH3, H2O). The reaction is catalyzed by sodium sulfite. The obtained products are suspected of being toxic substances which may be present in cosmetic matrices. Apparently, this reaction is a nucleophilic aromatic substitution but it may be explained by a mechanism involving a tautomeric form ...