Journal of the American Chemical Society p. 10722 - 10727 (1993)
Update date:2022-09-26
Topics:
Xu, Yiying
Dietze, Paul E.
The trifluoroethoxide-catalyzed trifluoroethanolysis and the hydroxide-catalyzed hydrolysis of a series of phenyldimethylsilyl ethers were examined. A Bronsted plot of the logarithm of the second-order rate constant KTFE for reaction with trifluoroethanol against the pKLG is not linear. The nonlinear plot might be taken as evidence for a change in rate-determining step of a reaction that proceeds through a pentavalent intermediate. However, the Bronsted plot for the hydroxide-catalyzed hydrolysis, where all the leaving groups are of lower pKa than hydroxide, has an identical shape as the Bronsted plot for the trifluoroethanolysis reaction. Therefore, the unusual shape of the Bronsted plots is not due to a change in rate-determining step. It is suggested that the results are most consistent with a one-step concerted mechanism and not with a mechanism involving a pentavalent intermediate.
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