2-(N-Methylanilino)-2-phenylthioacetonitrile: a useful reagent for preparation of conjugated α-amino alkenenitriles via tandem alkylation and dehydrosulphenylation

Abstract

Alkylation of the anion of 2-(N-methylanilino)-2-phenylthioacetonitrile 1 with halogenoalkanes resulted in concurrent elimination of benzenethiol to give conjugated α-aminoalkenenitriles of 2E-configuration. Counterattack by bromide and benzenethiolate ions was observed in the prolonged reactions of 1 with 1,4-dibromobut-2-ene and 3-bromo-1-(trimethylsilyl)prop-1-yne.