Remarkable Brönsted type correlation for base cleavage of carbon–silicon bonds. Kinetic isotope effects for interaction of carbanions with methanol

Abstract
The logarithms of the relative rates of cleavage of RSiMe3 compounds [R = 1-indenyl, 9-fluorenyl, 9-(2-bromofluorenyl), 9-(2,7-dibromofluorenyl), PhCC, Ph3C, Ph2CH, p-PhC6H4CH2, and PhCH2] by aqueous methanolic alkali correlate linearly with the pK's of the corresponding hydrocarbons R–H over a pKa range of 22 units; the ratio of RH/RD products obtained in 1:1 MeOH–MeOD is thought to be equal to the deuterium isotope effect for interaction of the carbanion R with methanol.