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.\ud Although carbonyl-assisted hydrolysis is the general rule, in compounds containing strongly electron-donating\ud groups, the ester function is directly attacked. The cause of rate enhancement in carbonyl-assisted hydrolysis\ud and in greater detail the case of 6-substituted derivatives are discussed. It is shown that the carbonyl-assisted\ud hydrolyses are characterized by decreased sensitivity to leaving-group structure. The implications of this result are\ud pointed out