Abstract The preparation of a collection of alkyl, aryl, and 1-alkenyl 2-(trimethylsilyl) ethyl sulfoxides is outlined, using mostly vinyltrimethylsilane or 2-(trimethylsilyl) ethanesulfenyl chloride (5) as key starting materials. The 2-(trimethylsilyl) ethyl group can be cleaved from many of the sulfoxides under oxidative fragmentation conditions using sulfuryl chloride and the reaction represents a new protocol for sulfinyl chloride synthesis. The method is ...