Mechanism of hydrolysis of coumaran-2-ones

David M. Heathcote, Gareth A. De Boos, John H. Atherton, Michael I. Page

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The hydrolysis of coumaran-2-one and 5-substituted 3-phenylcoumaran-2-ones is preceded by a pre-equilibrium involving the formation of an enolate anion at high pH. The pKa of 3-phenylcoumaran-2-one is 8.39 in water at 25°C and the 3-phenyl substituent increases the carbon acidity by 104. However, despite this ready carbanion formation, the conventional addition-elimination mechanism for hydrolysis of 3-phenylcoumaran-2-ones is confirmed by a solvent kinetic isotope effect of 0.63 and a Brønsted β1g of -0.6. This is compatible with rate limiting formation of a tetrahedral intermediate.

Original languageEnglish
Pages (from-to)535-540
Number of pages6
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number3
DOIs
Publication statusPublished - Mar 1998

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