Cyclic α-Acetoxynitrosamines: Mechanisms of Decomposition and Stability of α-hydroxynitrosamine and nitrosiminium ion reactive intermediates

L Chahoua, H Cai, JC Fishbein

Index: Chahoua, Latifa; Cai, Hongliang; Fishbein, James C. Journal of the American Chemical Society, 1999 , vol. 121, # 22 p. 5161 - 5169

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Citation Number: 24

Abstract

A study of the kinetics and mechanism of the decay of α-acetoxy-N-nitrosopyrrolidine and α- acetoxy-N-nitrosopiperidine are reported. The compounds differ in reactivity by more than 2 orders of magnitude at physiological pH. On the basis of thermodynamic parameters, common ion inhibition and azide ion trapping experiments, both compounds appear to decompose under these conditions by the formation of N-nitrosiminium ion intermediates. ...