Electrochemical synthesis of vicinal dithiocyanates from olefins and a thiocyanate salt in acidic media

The addition of electrochemically generated thiocyanogen to olefins is described. The effect of solvent and irradiation is briefly outlined. In acidic media the reaction takes place without irradiation. In acetic acid thiocyanogen adds smoothly to the double bond to produce the vicinal dithiocyanate. In methanol-HCl addition of both SCN and OCH3 takes place. An ionic mechanism analogous to halonium type addition reactions is proposed to account for the phenomena observed.