Reexamination of the mechanisms of decomposition of simple alpha-acetoxynitrosamines in the physiological pH range

The mechanism for the buffer independent decay of alpha-(acyloxy)nitrosoamines was examined. The rate constants of eight compounds were determined in the pH range 2-13. The results showed no measurable assistance in the decomposition of the Z forms of the alpha-(acyloxy)nitrosoamines. It is shown the even the simplest alpha-acetoxynitrosoamine decays with the intermediacy of an N-nitrosimium cation.