Aspects of tautomerism 12-Some causes and consequences of participation in the solvolysis of acid chlorides

Bhatt, Vivekananda M and Somayaji, Vishwanatha and Rao, Vishnumurthi M (1984) Aspects of tautomerism 12-Some causes and consequences of participation in the solvolysis of acid chlorides. In: Journal of Chemical Sciences, 93, Nu (4). pp. 593-600.

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Abstract

Solvolysis of nine representative half ester acid chlorides in aqueous acetone have been studied. Isomers solvolyse at distinctly different rates and furnish the original acids. Contrary to the well accepted views, no evidence for tautomerism or isomerism between the isomeric pairs of acid chlorides could be detected. In a number of cases alkoxy group participates in the solvolysis of neighbouring acid chlorides. This results in (a) rate enhancement and (b) partial or total shift of the reaction pattern from SN2 to SN1. Isomeric half ester acid chlorides, in the presence of a sufficiently strong Lewis acid, could give the same oxonium salt. Rearrangements observed in the reactions of unsymmetrical 1,2- and 1,3-dicarboxylic acid derivatives could be ascribed to the prior formation of common oxonium salt intermediates in the presence of Lewis acids.

Item Type:	Journal Article
Publication:	Journal of Chemical Sciences
Publisher:	Indian Academy of Sciences
Additional Information:	Copyright for this article belongs to Indian Academy of Sciences.
Keywords:	Tautomerism;solvolysis;acid chlorides.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	23 Oct 2009 04:48
Last Modified:	19 Sep 2010 05:44
URI:	http://eprints.iisc.ac.in/id/eprint/23138

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