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It is shown that vinyl sulfoxides undergo two novel modes of reactions induced selectively by the Ο-silylated ketene acetal used. Vinyl sulfoxides, on treatment with bulky tert-butyldimethylsilyl ketene acetals, undergo a Michael-Pummerer-type reaction to give γ-siloxy-γ- (phenylthio) esters, while with less bulky trimethylsilyl ketene acetals they undergo a double carbon-carbon bondforming reaction to give 3- (phenylthio) adipates. The reaction of related sulfoxides with Ο-silylated ketene acetals was also examined.
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Kita et al. (1987) studied this question.
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