Desulfonation of Vinyl Sulfones Utilizing β-Elimination of β-Stannyl Organosulfur Compounds

Abstract

A new method for desulfonation of vinyl sulfones utilizing organostannyl compounds is is reported. Vinyl sulfones, on treatment with (tributylstannyl) lithium in tetrahydrofuran at -78°C, give the Michael type addition products, βtributylstannyl sulfones, and their successive β-elimination by reaction with silica gel affords the desulfonated olefins in good yields. On the desulfonation of both of (E)-and (Z)-7-phenylsulfonyl-7--tetradecene [10 f] the (E)-7-tetradecene[15 f]is found to be a major product. Utilizing the procedure of this additionelimination sequence, the sulfonyl group of vinyl sulfones is substituted by electrophilic rea gents. Stereoselectivity of the reaction is also discussed.