Expeditious synthesis of beta-cycloacetalic sulfoxides. Introducing 1-phenylsulfinyl-2-phenylsulfanylethylene (SOSE), a promising new alkenylsulfur reagent

Abstract

In similarity with the strongly electrophilic BPSEs and despite its more electron-rich character, 1-phenylsul.nyl-2-phenylsulfanylethylene (SOSE) reacts with nucleophiles with displacement of the phenylthio moiety. Speci.cally it reacts with diols underbasic conditions to produce b-cycloacetalic sulfoxides. The reaction has been amply developed in carbohydrate chemistry