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Aspects of tautomerism. Part 16. Influence of the y-keto function on the reactions of sulphonic acids

Shashidhar, MS and Bhatt, MV (1989) Aspects of tautomerism. Part 16. Influence of the y-keto function on the reactions of sulphonic acids. In: Proceedings of the Indian Academy of Sciences - Chemical Sciences, 101 (4). pp. 319-326.

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Abstract

Reaction of sodium 2-formylbenzenesulphonate (1) with thionyl chloride or phosphorous pentachloride gives a mixture of pseudo (2) and normal (3) sulphonyl chlorides. Whereas ammonium 2-carboxybenzenesulphonate (6) gives only the normal sulphonyl chloride (7) on reaction with thionyl chloride, a mixture of normal (7) and pseudo (8) isomers are formed on reaction with phosphorous pentachloride. Sodium 2-benzoylbenzenesulphonate (15), on the other hand, gives the corresponding normal sulphonyl chloride (16) on reaction with both of the reagents mentioned above. Based on these observations it is concluded that γ-keto sulphonic acids are amenable to the influence of γ-carbonyl group as in the case of γ-keto carboxylic acids but to a lesser extent. © 1989 Indian Academy of Sciences.

Item Type: Journal Article
Additional Information: Copyright of this article belongs to Indian Academy of Sciences.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Date Deposited: 20 Jul 2010 07:39
Last Modified: 20 Jul 2010 07:39
URI: http://eprints.iisc.ernet.in/id/eprint/30371

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