Novel synthesis of 3,4-diaminobutanenitriles and 4-amino-2-butenenitriles from 2-(cyanomethyl)aziridines through intermediate aziridinium salts: An experimental and theoretical approach

1-Arylmethyl-2-(cyanomethyl)aziridines are transformed into 4-(N,N-bis(arylmethyl)amino)-3-(pyrrolidin-1-yl)butanenitriles and 4-(N,N-bis(arylmethyl)amino)-2-butenenitriles through 4-(N,N-bis(arylmethyl)amino)-3-bromobutanenitriles in high yields. The main steps have involved the unprecedented regiospecific ring opening of intermediate 2-(cyanomethyl)aziridinium salts by bromide and pyrrolidine in acetonitrile at the substituted aziridine carbon atom.