ASPECTS OF TAUTOMERISM .7. STUDY OF KETO PARTICIPATION IN ALKALINE-HYDROLYSIS OF NORMAL ESTERS OF GAMMA-KETO ACIDS

Study of the alkaline hydrolysis of a number of variously substituted normal o-benzoylbenzoic esters has been reported. Although carbonyl-assisted hydrolysis is the general rule, in compounds containing strongly electron-donating groups, the ester function is directly attacked. The cause of rate enhancement in carbonyl-assisted hydrolysis and in greater detail the case of 6-substituted derivatives are discussed. It is shown that the carbonyl-assisted hydrolyses are characterized by decreased sensitivity to leaving-group structure. The implications of this result are pointed out. © 1979, American Chemical Society. All rights reserved.