Stereospecific Reductive Desulfinylation of 1-Aryl-2-(methylsulfinyl)-2-(methylthio)ethenes with Grignard Reagents

Article abstract of DOI:10.1246/bcsj.55.3669

(E)-1-Aryl-2-(methylsulfinyl)-2-(methylthio)ethene, obtained by the Knoevenagel-type condensation of methyl (methylthio)methyl sulfoxide with the corresponding aromatic aldehyde, was found to react with ethylmagnesium chloride to give (Z)-1-aryl-2-(methylthio)ethene predominantly.Since the reaction of (Z)-1-(methylsulfinyl)-1-(methylthio)-2-phenylethene afforded (E)-1-(methylthio)-2-phenylethene, the present reaction appeared to be stereospecific.