Journal of the American Chemical Society p. 5962 - 5964 (1986)
Update date:2022-08-04
Topics:
Washburn, William N.
Cook, Ewell R.
Kinetic and 18O-labeling studies demonstrate that in the hydrolysis of nonenolizable acetoacetate esters, the carbonyl hydrate acts as a nucleophilic catalyst.A cyclic four-membered lactone is formed and later opens.Structure/reactivity studies showed the rate-determining step to be a function of the pKa of the leaving group and the substituent bound to C3 of the acetoacetate residue.Rate accelerations of 4 to E4 were observed for hydrolyses of the corresponding p-nitrophenyl esters, depending on the substituent at C3.
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