Use of trichloroacetonitrile as a hydrogen chloride generator for ring-opening reactions of aziridines†
Yasunori Toda,Riki Matsuda,Shuto Gomyou,Hiroyuki Suga
Organic & Biomolecular Chemistry Pub Date : 03/21/2019 00:00:00 , DOI:10.1039/C9OB00602H
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.

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