YAKUGAKU ZASSHI
Online ISSN : 1347-5231
Print ISSN : 0031-6903
ISSN-L : 0031-6903
Degradation of Phenylsulfonyl-5, 5-diphenylhydantoins
AKIO KOBAYASHISUSUMU UMEMOTO
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1969 Volume 89 Issue 11 Pages 1549-1552

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Abstract
Examinations were made on the decomposition reaction of 3-phenylsulfonyl-(I), 1-phenylsulfonyl-(II), and 1, 3-bis(phenylsulfonyl)-5, 5-diphenylhydantoin (III) with sodium hydroxide, hydrochloric acid, or amines. It was found that I, II, and III differed in stability and direction of decomposition. I was comparatively easily decomposed, especially when treated with sodium hydroxide, and underwent cleavage at 1-2 and 3-4 positions even at room temperature, while heating with dilute hydrochloric acid effected liberation of phenylsulfonyl group and cleavage between 3 and 4 positions. Heating with amines resulted in cleavage of 3-4 position. II was very stable but underwent cleavage at 2-3 position when heated with conc. sodium hydroxide over a long period. The phenylsulfonyl group in 3-position of III was very easily liberated, forming II when heated with dil. sodium hydroxide, hydrochloric acid, or amines.
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