Abstract
The mechanism of the reaction of β-lactones (2-oxetanones) with potassium alkoxides in aprotic solvents was investigated. Despite previous suggestions, the attack of alkoxide ion occurs on the carbonyl carbon atom of β-lactones, cleaving the acyl-oxygen bond to yield the corresponding potassium alcoholate of the respective β-hydroxycarboxylic acid ester. Next, the saturated ester is formed due to potassium hydroxide elimination. The nature of the alkoxide used and complexation of alkali metal cation by crown ether have no significant effect on the reaction course in aprotic solvents
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