The solvolysis of N-acetoxy-2-acetylaminofluorene and N-acetoxy-4-acetylaminobiphenyl: delicate balance between nitrenium ion formation and hydrolysis

GR Underwood, RB Kirsch

Index: Underwood, Graham R.; Kirsch, Robert B. Journal of the Chemical Society, Chemical Communications, 1985 , # 3 p. 136 - 138

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Citation Number: 12

Abstract

The solvolysis of N-acetoxy-2-acetylaminofluorene in aqueous acetone at neutral pH proceeds exclusively with nitrenium ion formation while under the same conditions, the 4-aminobiphenyl analogue undergoes exclusive acyl-oxygen scission. ... Many polycyclic aromatic amines and amides are known mutagens or carcinogens.' Of these, the most extensively studied is 2-acetylaminofluorene. It is generally regarded that these compounds owe their biological ...