Efficient regio- and stereo-selective cleavage of aziridines and epoxides using an ionic liquid as reagent and reaction medium

Abstract

Ionic liquids, containing a variety of functionalities such as halo, azido, and thiocyano, efficiently cleave aziridines and epoxides to the corresponding products in high yields. The cleavages are regio- and stereo-selective. The reactions are complete in 1 h at 60 °C and do not require any other catalyst or organic solvent. Thus, a convenient synthetic route to 1,2-haloamines, 1,2-azidoamines, 1,2-thiocyanoamines, 1,2-azidoalcohols, and 1,2-thiocyanoalcohols is developed.Key words: aziridine, epoxide, ionic liquid, cleavage, regioselectivity, stereoselectivity