Shashidhar, M. S. ; Bhatt, M. V. (1989) Aspects of tautomerism. Part 16. Influence of the γ-keto function on the reactions of sulphonic acids Proceedings of the Indian Academy of Sciences - Chemical Sciences, 101 (4). pp. 319-326. ISSN 0253-4134
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Official URL: http://www.ias.ac.in/j_archive/chemsci/101/2/319-3...
Related URL: http://dx.doi.org/10.1007/BF02840664
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.
Item Type: | Article |
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Source: | Copyright of this article belongs to Indian Academy of Sciences. |
Keywords: | Ring-chain Tautomerism; Neighbouring Group Effect; Neighbouring Group Participation |
ID Code: | 2682 |
Deposited On: | 08 Oct 2010 08:41 |
Last Modified: | 16 May 2016 13:37 |
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