Reaction of [arylthio(chloro)methyl]trimethylsilanes with arenes and alk-1-enes in the presence of Lewis acid: syntheses of [aryl(arylthio)methyl]- and (1-arylthioalk-3-enyl)-trimethylsilanes

Abstract

Treatment of equimolar amounts of the [arylthio(chloro)methyl) trimethylsilanes (2) or (3) and electron-rich arenes with an equimolar amount of Lewis acid (SnCI₄ or TiCI₄) gave the Friedel-Crafts reaction products, [aryl (arylthio)methyl] trimethylsilanes (4) or (5), in high yields. Similar treatment of the chlorides (2) or (3) with alk-1-enes gave ene type products, (1-arylthioalk-3-enyl]trimethylsilanes (12) or (13), in moderate yields. Some chemical transformations of these products are also described.