The factors determining the kinetic and thermodynamic stabilities of N-chlorohydrazines are discussed. Acyclic N-chlorohydrazines exist only as trialkyldiazenium chlorides 3a, b. Chlorination of 2-acyl-1, 1-dimethylhydrazines 6a, b gave 1, 4-diacyl-2, 3- dimethylhexahydro-1, 2, 4, 5-tetrazines 7a, b via hydrazyl radical intermediates, and chlorination of a 1-phenylpyrazolidin-5-one 8 gave phenylazoisovaleric esters 9a, b. ...