Open-chain nitrogen compounds. Part III. The formation of triazenes in the reaction of diazonium salts with α-aminoacetonitrile and related α-substituted alky lamines

Abstract

Several triazenes of type Ar•N==N•NH•CH2Y, where Y is electron withdrawing, have been prepared by reaction of the diazonium salts X•C6H4N2+ (X = H, p-NO2, p-CO2Me, p-COPh, and o-COPh) with the α-substituted alkylamines NH2CH2Y (Y = CN, CO2Et, COPh, and CH(OCH3)2) in aqueous solution, without prior isolation of the diazonium salt. In all cases, the diazonium ion attacks at the NH2 moiety exclusively and the methylene group in NH2CH2Y shows no tendency to compete for the diazonium ion.