Journal of the American Chemical Society p. 3685 - 3687 (1982)
Update date:2022-08-16
Topics:
Burt, R. A.
Chiang, Y.
Kresge, A. J.
McKinney, M. A.
The rate constant for the hydronium ion catalyzed hydrolyis of trimethyl orthocyclopropanecarboxylate measured in dilute aqueous HCl, kH+=5300 M-1s-1, was found to be different from that measured in buffer solutions at pH 6-8, kH+=81 00 M-1s-1.This difference is similar to that observed for cyclic ortho esters and is taken as evicence for a change in the reaction mechanism from rate-determining conversion of ortho ester to a dialkoxycarbonium ion intermediate at high pH to rate-determining decomposition of the hydrogen ortho ester formed by hydration of this ion at low pH.Discovery of this mechanistic change in this acyclic system suggests that this is a general phenomenon common to all ortho esters substituted with carbication-stabilizing groups at their pro-acyl carbon atoms.
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