Abstract
The kinetics and mechanism of the hydrolysis of tetrahydro-2-furyl and tetrahydropyran-2-yl alkanoates in water and water–20% ethanol are reported. In acidic and neutral media, kinetics, activation parameters, 18O isotope exchange studies, substituent effects, solvent effects and the lack of buffer catalysis point clearly to an AA1-1 mechanism with formation of the tetrahydro-2-furyl or tetrahydropyran-2-yl carbonium ion as the rate-limiting step. There is no evidence of a base-promoted BAC-2 mechanism up to pH 12.
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Schedule a callMore From: Journal of the Chemical Society, Perkin Transactions 2
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