The reaction of pentacyanonitrosylferrate(II) with primary amines as a source of stabilized aliphatic diazonium ions: A new route to secondary amines

Article abstract of DOI:10.1016/S0040-4039(99)00810-2

Pentacyanonitrosylferrate(II), 1, reacts with n-butylamine to produce di-n-butylamine in high yields (81-95%). The absence of rearranged products indicates that the initially produced diazonium ion is stabilized by coordination to the metal. Benzylamine and 1,4-diaminobutane react with 1 to produce dibenzylamine and piperidine, respectively.