Ambident Reactivities of Carbenium Salts Possessing a Thiocarbonyl Group at the (beta)-Position

A stable, crystalline carbenium iodide, which possesses a thiocarbonyl group at the (beta)-position, shows ambident reactivities, thereby reacting with a hard nucleophile OH- at the carbenium carbon atom and with a soft nucleophile RLi at the thiocarbonyl sulfur atom. Thermal dissociation of the MeLi adduct to a carbene and a ketene dithioacetal is also presented