Tetrahedral intermediates formed by nitrogen and oxygen attack of aromatic hydroxylamines on acetyl cyanide

…, MM Marques, S Prabhakar, HS Rzepa

Index: Lobo, Ana M.; Marques, M. Matilde; Prabhakar, Sundaresan; Rzepa, Henry S. Journal of Organic Chemistry, 1987 , vol. 52, # 13 p. 2925 - 2927

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Citation Number: 28

Abstract

Aromatic hydroxylamines 1 have been postulated as intermediates in the carcinogenic process induced by some aromatic amines. The necessary chemical activation of 1 for the latter stages of this process can subsequently be achieved by 0-acylation, rendering the N-0 bond labile for cleavage and reaction with DNA bases. 2 We have discovered that aromatic hydroxylamines react with aroyl cyanides at room temperature to afford in almost ...