The mechanism of solvolysis of (2-bromoethyl)trimethylsilane. Evidence for the migration of the trimethylsilyl group

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Abstract

When solvolysis of the bromide Me3SiCH2CD2Br by aqueous methanol is allowed to proceed to about 50% completion, the recovered bromide contains Me3SiCD2CH2Br and Me3SiCH2CD2Br, in 1 2 ratio. This migration of the Me3Si group is consistent with a mechanism involving anchimerically assisted ionization of the CBr bond to give a silacyclopropenium ion. © 1970.

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Cook, M. A., Eaborn, C., & Walton, D. R. M. (1970). The mechanism of solvolysis of (2-bromoethyl)trimethylsilane. Evidence for the migration of the trimethylsilyl group. Journal of Organometallic Chemistry, 24(2), 301–306. https://doi.org/10.1016/S0022-328X(00)80268-5

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