Synthesis of Polyfluorinated Tertiary Alcohols Using Ring Opening Reactions of 2,2-Bis(trifluoromethyl)oxirane [1]

Abstract

This paper describes new reactions of 2,2-bis(trifluoro­methyl)oxirane (1). Ring opening of 1 by oxygen, nitrogen, sulfur or carbon nucleophiles (Nu^-) proceeds regioselectively, with exclusive formation of tertiary alcohols: NuCH₂C(CF₃)₂OH. The reaction of 1 with strong acids (HX) is also regioselective and proceeds under mild conditions leading to the formation of XCH₂C(CF₃)₂OH (X = FSO₂O, CF₃SO₂O, Cl, I). The addition of acetic acid to 1, however, requires an elevated temperature and TaF₅ a catalyst. Highly selective reactions of 1 with nucleophilic or electrophilic reagents provide a simple and general route to materials containing CH₂C(CF₃)₂OH group.

Key words - 2,2-bis(trifluoromethyl)oxirane - ring opening reactions - nucleophilic addition - electrophilic addition - epoxides

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