Competition between neighbouring-group participation by carbonyl groups and carbon acids in ester hydrolyses
Abstract
The alkaline hydrolyses of methyl 8-acyl- and 8-aroyl-1-naphthoates have been examined: intramolecular catalysis by the neighbouring carbonyl group occurs for the 8-formyl and 8-(3′- and 4′-substituted benzoyl)esters; whereas, the 8-acetyl, 8-propionyl, and 8-iso-butyryl esters display catalysis by the neighbouring carbon acid.