Reactions of novel mono- and difluoroacetyltrialkylsilanes with sulfur and phosphorus ylides |
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| Authors: | Silvana C NgoWoo Jin Chung Dong Sung LimSeiichiro Higashiya John T Welch |
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| Affiliation: | Department of Chemistry, University at Albany, State University of New York, 1400 Washington Ave., Albany, NY 12222, USA |
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| Abstract: | The reactions of difluoroacetyltrialkylsilanes with methylidene triphenylphosphorane and benzylidene triphenylphosphorane are affected by the nature of the silyl substituents giving either the enol silyl ether or normal Wittig product exclusively, or mixture of both. Reactions with Horner-Emmons type ylide gave only the alkene products. Reactions of mono- and difluoroacetyltrialkylsilanes with dimethylsulfoxonium methylide gave the enol silyl ether products exclusively. Conversion of an enol silyl ether to an epoxide was effected with m-CPBA. |
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| Keywords: | Fluorinated acetylsilanes Wittig reaction Horner-Emmons reaction Ylides Dimethylsulfoxonium methylide Enol silyl ether |
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