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

Org Biomol Chem

Department of Materials Chemistry, Faculty of Engineering, Shinshu University, 4-17-1 Wakasato, Nagano 380-8553, Japan.

Published: April 2019

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.

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http://dx.doi.org/10.1039/c9ob00602hDOI Listing

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