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: NuCH2 C(CF3 )2 OH. The reaction
of 1 with strong acids (HX) is also regioselective
and proceeds under mild conditions leading to the formation of XCH2 C(CF3 )2 OH (X = FSO2 O,
CF3 SO2 O, 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 CH2 C(CF3 )2 OH
group.
Key words
- 2,2-bis(trifluoromethyl)oxirane - ring opening reactions - nucleophilic addition - electrophilic
addition - epoxides
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