The Enol Silyl Ether of 3, 3, 3-Trifluoropropiophenone Preparation and Carbon-Carbon Bond Forming Reactions

Abstract

The title enol silyl ether [3] was readily prepared from 3, 3, 3-trifluoropropiophenone with trimethylsilyl triflate, and its reactions with a variety of carbon-electrophiles were studied. The silyl ether [3] was found to react with benzaldehyde acetal, benzaldehyde, and chloromethyl ethyl ether, whereas [3] did not undergo the expected C-C bond formation with aliphatic acetal, aliphatic aldehyde, and acyl chloride.
The unique reactivity of [3] was compare d with those of the non-fluorinated counterpart and the enol silyl ether of methyl 3, 3, 3-trifluoropropionate.