Use of trichloroacetonitrile as a hydrogen chloride generator for ring-opening reactions of aziridines

Abstract

Regioselective ring-opening reactions of 2-aryl-N-tosylaziridines are described, in which hydrogen chloride is generated by photodegradation of trichloroacetonitrile. HCl adducts are obtained in high yields in 1,4-dioxane, whereas methanol adducts are predominantly obtained in methanol. Trichloroacetonitrile can serve as a photoresponsive molecular storage generator for hydrogen chloride.