Alpha-lithiosilanes: III. The Reaction of Vinylalkoxysilanes with Organolithium Reagents |
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Authors: | Paul Ronald Jones Thomas F.O Lim Mark L McBee Richard A Pierce |
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Affiliation: | Department of Chemistry, North Texas State University, Denton, Texas 76201, U.S.A. |
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Abstract: | The reaction of two equivalents of vinyldimethylethoxysilane or vinyldimethylmethoxysilane with hydrocarbon soluble alkyllithium reagents; -BuLi, -BuLi, or -BuLi; in hexane at low temperature gives high yields of 1,1-dimethyl-2-alkyl-4-(dimethylalkoxysilyl)silacyclobutanes. With methyl- or phenyllithium substituted vinylsilanes are obtained. The stereochemistry of the silacyclobutanes is assigned on the basis of Si-29 and H-1 NMR. For vinyldimethylethoxysilane the ratio of cis to trans silacyclobutane is about , and is independent of the alkyllithium reagent used. In the reaction of vinyldimethylmethoxysilane with -BuLi a ratio of the cis and trans silacyclobutane is obtained. A pathway is proposed which is consistent with the stereochemical results and with the products isolated in the reaction run in THF. |
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