Abstract
Abstract Sulfinic esters react with methylsulfinylcarbanion to give the corresponding α-methylsulfinylmethyl sulfoxides(I) in good yields. The per cent ratio of meso form to dl form of the product obtained is about 60 : 40. When (−)-menthyl (−)-(S)-p-toluenesulfinate is treated with methylsulfinylcarbanion, dextrorotatory α-methylsulfinylmethyl p-tolyl sulfoxide(IIa) is obtained. Recrystallization of (IIa) yields the diastereomerically pure (+)-(S)-α-methylsulfinyl-(R)-methyl p-tolyl sulfoxide(IIb). Based on these observations, the stereochemistry of the reaction is discussed.
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