Reactions of 3-chloropentafluoropropene-1,2-oxide with bifunctional nucleophiles: a new route to chlorodifluoromethyl-substituted heterocycles

An optimized preparation of 3-chloropentafluoropropene-1,2-oxide via alkaline peroxide epoxidation of 3-chloropentafluoro-1-propene under phase transfer catalysis conditions is described. The title epoxide was reacted with various bifunctional nitrogen nucleophiles to give five-, six- and seven-membered-ring heterocycles with pendant chlorodifluoromethyl groups. The described methodology represents a novel approach to chlorodifluoromethylated heterocycles.