Acyl anion equivalents. Synthesis of ketones and α-(phenylthio)ketones from the adducts of bis(phenylthio)carbanions and carbonyl compounds

Abstract

Bis(phenylthio)carbanions react with aldehydes and ketones to give α-hydroxybis(phenylthio)acetals. The aldehyde adducts give simple ketones with trifluoroacetic acid and α-(phenylthio) ketones with toluene-p-sulphonic acid. The effect of these reagents on the ketone adducts is also discussed. The mechanisms and scope of all the reactions are described. The synthesis of α-(phenylthio)ketones is regiospecific and makes these compounds available as specific enol equivalents.