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, benzalolehyde, and ehloro-methyl ethyl ether, whereas [5] did not undergo the expected C-C bond formation with aliphatic acetal, aliphatic aldehyde, and acyl chloride. The unique reactivity oft [3] was compared with those of the non-fluorinated counterpart and the enol silyl ether of methyl 3, 3, 3-trifluoropropionate. © 1985, The Chemical Society of Japan. All rights reserved.