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Aspects of tautomerism. 6. Base-catalyzed hydrolysis of pseudo esters of .gamma.-keto acids

Bhatt, M Vivekananda and Rao, K Sundararaja and Rao, G Venkoba (1977) Aspects of tautomerism. 6. Base-catalyzed hydrolysis of pseudo esters of .gamma.-keto acids. In: Journal of Organic Chemistry, 42 (16). pp. 2697-2702.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo00436a009

Abstract

The rates of base-catalyzed hydrolysis of pseudo esters derived from y-keto acids show strikingly poor sensitivity to the nature of the leaving group.la The rates vary in the narrow range of about 12-fold as contrasted to a 103-fold spread of the corresponding benzoate esters. The results presented are consistent with a rate-determining formation of a tetrahedral intermediate (11) and i t s rapid collapse, by the cleavage of the lactone ring in a fast step.

Item Type: Journal Article
Additional Information: copyright of this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 19 Oct 2009 13:11
Last Modified: 19 Sep 2010 05:50
URI: http://eprints.iisc.ernet.in/id/eprint/24431

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