N-Nitroso- and N-Nitrotrialkylureas and Their Decomposition

Article abstract of DOI:10.1021/jo00199a023

The synthesis and decomposition of N-(n-butyl)-N',N'-dimethyl-N-nitrosourea (2a), N-(n-butyl)-N',N'-dimethyl-N-nitrourea (3a), N',N'-dimethyl N-(1-norbornyl)-N-nitrosourea (2b), N',N'-dimethyl-N-(1-norbornyl)-N-nitrourea (3b) are described.Several of the compounds show complex NMR spectra ascribable to rotational isomerism.Decomposition of 2a and 3a gave n-butyl N,N-dimethylcarbamate and tetramethylurea, while decompostion of 2b and 3b in methylene chloride gave 1-norbornyl N,N-dimethylcarbamate and 1-norbornyl chloride.These products are formed via diazotic acid derivatives and carbonium ion pairs; the reaction mechanism is essentially the same as that established for the closely related N-nitrosoamides.In concentrated solutions, nitrosourea 2a yielded a new product, amino acid 20.