Chemistry of O-Silylated Ketene Acetals: Preparation of α-Siloxy Phenyl Sulfides and Methyl 3-(Phenylthio)butyrates from Alkyl Phenyl Sulfoxides
Treatment of alkyl phenyl sulfoxides (2a-h) with O-methyl-O-tert-butyldimethylsilyl ketene acetal (1a) in dry acetonitrile in the presence of a catalytic amount of zinc iodide caused a Pummerer-type rearrangement to give α-siloxy phenyl sulfides (3a-h) under mild conditions.On the oder hand, treatment of the sulfoxide (2d) with O-methyl-O-trimethylsilyl ketene acetals (1b,c) under similar conditions gave carbon-carbon bond-formed products, methyl 3-(phenylthio)-butyrates (8 and 9).Keywords - O-methyl-O-tert-butyldimethylsilyl ketene acetal; alkyl phenyl sulfoxide; Pummerer rearrangement; α-siloxy phenyl sulfide; O-methyl-O-trimethylsilyl ketene acetal; carbon-carbon bond forming reaction; methyl 3-(phenylthio)butyrate; α-siloxy sulfide reaction