Abstract
Abstract Homolytic addition of thiocyanogen to alkenes with at least three methyl groups or two phenyl groups on the double bond gives vicinal dithiocyanates and/or thiocyanato-isothiocyanates. The addition to (E)- and (Z)- PhCH=CHPh is non-stereospecific, but the thiocyanato-isothiocyanates derived from unsymmetrical alkenes are formed regiospecifically with the isothiocyanato group being attached to the more heavily substituted C atom. A radical-chain mechanism, involving competing kinetically-controlled chain transfer at the S atom and sterically-controlled chain transfer at the N atom of the thiocyanogen molecule, is proposed.
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