Aspects of tautomerism. Part 16. Influence of the y-keto function on the reactions of sulphonic acids |
| |
Authors: | M. S. Shashidhar and M. V. Bhatt |
| |
Affiliation: | (1) Department of Organic Chemistry, Indian Institute of Science, 560012 Bangalore, India |
| |
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. |
| |
Keywords: | Ring-chain tautomerism neighbouring group effect neighbouring group participation |
本文献已被 SpringerLink 等数据库收录! |