Photolysis of Vinyl Halides. Reaction of Photogenerated Vinyl Cations with Cyanate and Thiocyanate Ions

Article abstract of DOI:10.1021/jo00293a025

The title reaction was conducted in a two-phase system of dichloromethane and water using a tetrabutylammonium halide as a phase-transfer catalyst.The reaction of the photogenerated arylvinyl cation with cyanate ion gave only isoquinolone derivatives, whereas the reaction with thiocyanate ion afforded products derived from S attack, vinyl thiocyanates, and products derived from N attack, vinyl isothiocyanates or thioisoquinolones.The ambident nature of thiocyanate ion is compared with the reaction of benzyl bromides.