Journal of the Chemical Society. Perkin transactions II p. 557 - 562 (1988)
Update date:2022-08-17
Topics:
Isaacs, Neil S.
Najem, Tariq S.
Hydrolyses of esters which possess an acidic proton at the α or vinylogous position can, in principle, hydrolyse by the E1cb route via a ketenoid intermediate.To the kinetic evidence for such a mechanism in the hydrolyses of 4-hydroxybenzoates, malonates, acetoacetates and fluorenecarboxylates is now added the further criterion of volumes of activation.Values of ΔV(excit.) for reactions proceeding by the E1cb route are positive and contrast with the negative values associated with hydrolyses by the more usual BAc2 mechanism.
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