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

Add time:07/18/2019    Source:sciencedirect.com

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 12 ratio. This migration of the Me3Si group is consistent with a mechanism involving anchimerically assisted ionization of the CBr bond to give a silacyclopropenium ion.

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