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Synthesis 2002(15): 2225-2231
DOI: 10.1055/s-2002-34857
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Viacheslav A. Petrov*
DuPont Central Research and Development, Experimental Station, P.O. Box 80328, Wilmington, Delaware 19880-0328, USA
e-Mail: Viacheslav.A.Petrov@USA.Dupont.com;
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Publication History

Received 24 May 2002
Publication Date:
21 October 2002 (online)

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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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Publication No.: 8286.

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Grushin, V. V.; Marshall, W. J.; Halliday, G. A.; Davidson, F.; Petrov, V. A. J. Fluorine Chem., in press.