Journal of the Chemical Society. Perkin transactions I p. 969 - 976 (1981)
Update date:2022-08-03
Topics:
Fleming, Ian
Floyd, Christopher D.
Tris(trimethylsilyl)methyl-lithium (1) reacts with non-enolisable aldehydes, ketones, and acid chlorides, and with some epoxides, with the formation of carbon-carbon bonds.This method of preparing functionalized silanes is limited by the readiness with which (1) abstracts a proton, if one is available, rather than attack at carbon.In the reaction with epoxides, the product alkoxide can transfer a silyl group from carbon to oxygen, and in one case the intermediate so formed reacts to give a cyclopropane (32) in what is a homologue of the Peterson reaction.The 1,4-transfer of a silyl group occurs in other systems when the resulting carbanion is stabilised by such groups as phenylthio and diphenylphosphinoyl.
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Doi:10.1248/cpb.29.370
(1981)Doi:10.1039/P19810001132
(1981)Doi:10.1016/j.carbpol.2011.09.071
(2012)Doi:10.1016/S0008-6215(00)86026-7
(1981)Doi:10.1007/BF00949602
(1981)Doi:10.1021/jo00335a037
(1981)
