ELECTROLYTIC PARTIAL FLUORINATION OF ORGANIC-COMPOUNDS .17. REGIOSPECIFIC ANODIC FLUORINATION OF SULFIDES BEARING ELECTRON-WITHDRAWING SUBSTITUENTS AT THE POSITION-ALPHA TO THE SULFUR ATOM

Regiospecific monofluorination of various sulfides bearing electron-withdrawing substituents, cyano, ester, acyl, amino, and phosphonate groups,at their alpha-positions was successfully carried out by the anodic oxidation of the sulfides in Et(3)N . 3HF/MeCN using an undivided cell. Fluorine was introduced at the position alpha to the sulfur atom selectively. Fluorination of alpha-(phenylthio)-substituted cyclic carbonyl compounds was also successful. Furthermore, anodic alpha,alpha-difluorination of ethyl alpha-(phenylthio)acetate was also successfully carried out although a large amount of electricity was required.