Aspects of Tautomerism. 13. Alkaline Hydrolysis of γ-, δ-, and ε-Keto Esters and their Desoxy Analogues. Geometrical Constraints on Keto Participation

Article abstract of DOI:10.1021/jo00191a024

The rates of alkaline hydrolysis of methyl β-benzoylpropionate (I), methyl γ-benzoylbutyrate (II) and methyl δ-benzoylvalerate (III) decrease in the order I>II>III.Keto participation is the predominant pathway in the case of γ-keto esters.Evidence has also been obtained for keto participation in the case of δ-keto esters, whereas no such evidence is available in the case of ε-keto esters studied.