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How Is 1,1-Dimethyl-1-Silacyclopent-2-Ene Formed in the Addition of Dimethylsilylene To 1,3-Butadiene? Evidence for a Pathway Via a Vinylsilirane Intermediate

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Addition of dimethylsilylene Me2Si: to 1,4-dideutero-1,3-butadiene in gas-phase flow pyrolysis experiments leads to the formation of 2,5-dideutero-1,1-dimethyl-1-silacyclopent-3-ene and 4,5- dideutero-1,1-dimethyl-1-silacyclopent-2-ene. Pyrolysis of the silacyclopent-3-ene product leads to the same silacyclopent-2-ene. This labelling pattern for the silacyclo-pent-2-ene product is compelling evidence for its formation via carbon-carbon bond-cleavage in a vinylsilirane intermediate, and for the intermediacy of the vinylailirane in the silylene addition leading to the silacyclopent-3-ene as well.

Affiliations: 1: Department of Chemistry Washington University Saint Louis, Missouri 63130 U.S.A.


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