Transnitrosation by nitrosamines and nitrosoureas.

The factors that determine alicyclic nitrosamines can act as transnitrosating agents include steric and electronic factors, as well as factors relating to the basicity of the parent amine. The slower transnitrosating agents, such as nitrosopipecolic acid, can nitrosate piperidine at pH 1.7, while the nitrosopiperazines cannot. Nitrosoureas, particularly nitrosotrialkylureas, are rapid transnitrosating agents and all are capable of nitrosating piperidine to high yields, even at pH 3.6.