Trimethylhalosilane elimination from trimethylsilylsubstituted gem-dihalocyclopropanes

Article abstract of DOI:10.1016/S0022-328X(00)92645-7

The aluminum halide-catalyzed elimination of trimethylhalosilane from 1,1-dihalo-2-(trimethylsilyl)cyclopropanes (XCl and Br) resulted in the formation of propargyl halides, HCCCH₂X. Reaction of 1,1-dichloro-2,2-dimethyl-3-(trimethylsilyl) cyclopropane with sodium ethoxide in ethanol also resulted in elimination of trimethylchlorosilane; the organic product was 3-ethoxy-3-methyl-1-butyne, HCCCMe₂OEt, and a mechanism involving β-elimination of trimethylchlorosilane to give 1-chloro-3,3-dimethylcyclopropene and reaction of the latter to produce the acetylenic ether is suggested.