The Reaction of Polyhalides with Allylsilanes Catalyzed by Copper(I) Chloride

Article abstract of DOI:10.1246/bcsj.70.3055

Allyltrimethylsilane reacted with polyhalogen compounds in the presence of copper species, such as copper(I) chloride, copper(II) chloride or metallic copper, to form polyhalo compounds containing an allyl group. Other allylsilane derivatives than allyltrimethylsilane were also subjected to a reaction with carbon tetrachloride. 3-Chloro- or 3-bromo-3-trimethylsilyl-1-propene gave 4,4,4-trichloro-1-trimethylsilyl-1-butene. Ethyl 1-trimethylsilylallyl carbonate afforded ethyl 4,4,4-trichloro-1-butenyl carbonate along with a hydrotrichloromethylation product. 2-Methyl-3-trimethylsilyl-1-propene yielded a product based on the addition of a trichloromethyl group followed by hydrogen-elimination from a 2-methyl group.