Generation and trapping of cyclopropyldiazonium and diazocyclopropane in the nitrosation of cyclopropylamine with alkyl nitrites

Diazocyclopropane and an cyclopropyldiazonium ion, which are highly reactive intermediates, can be generated and trapped by appropriate substrates immediately in the direct nitrosation of cyclopropylamine with alkyl nitrites. Diazocyclopropane is trapped by unsaturated compounds to form the corresponding 1,3-dipolar cycloadducts, while cyclopropyldiazonium reacts with reactive arenes and CH acids (e.g., malononitrile) to give azo compounds. It was shown that both cyclopropyldiazonium and diazocyclopropane in equilibrium can be simultaneously trapped in the presence of equimolar amounts of 2-naphthol and acrylonitrile or methyl methacrylate.