Reactions of carbanions of dimethyl sulfoxide and dimethyl sulfone with isocyanates, isothiocyanates, and other electrophilic reagents. Preparation of. beta.-amido …

M Von Strandtmann, S Klutchko…

Index: von Strandtmann,M. et al. Journal of Organic Chemistry, 1971 , vol. 36, p. 1742 - 1744

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Abstract

In the case of isothiocyanates the sole isolable products were the P-thioamido sulfoxides (Table I, type C). Apparently, because of the lesser electronegativity of sulfur as compared to oxygen, the methylene group of the primary product is insufficiently acidic to undergo reaction with a second mole of the isothiocyanate. The opposite effect was observed during the reaction of phenyl isocyanate with the anion of dimethyl sulfone.

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