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

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    • Keywords


      Ring-chain tautomerism; neighbouring group effect; neighbouring group participation

    • 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.

    • Author Affiliations


      M S Shashidhar1 M V Bhatt1

      1. Department of Organic Chemistry, Indian Institute of Science, Bangalore - 560012, India
    • Dates

  • Journal of Chemical Sciences | News

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