Abstract
The alkaline hydrolysis of 2-thioxo-5-arylidenehydantoins (R = p-NO2, p-Br, H, p-Me, and p-OMe) and their mono- and dialkyl derivatives proceeds with the formation of arylpyruvic acids, which undergo subsequent decomposition in the presence of oxygen in alkali solutions. 2-Thioxohydantoin, thioparabanic acid, and thiourea were not detected among the reaction products. Side processes involving the oxidation of the thioxohydantoins also take place under these conditions. The rate of hydrolysis of 2-thioxo-5- arylidenehydantoins varies as the concentration of alkali in solution changes, and the log k = f (CKOH) dependence is S-shaped. The hydrolysis of nonionized hydantoins and their monoanions is a bimolecular reaction and is first-order in substrate and hydroxide ion. The rate-determining step in the hydrolysis is the addition of hydroxide ion to the carbon atom of the C4=O group.
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See [1] for communication 17.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 406–412, March, 1979.
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Ivin, B.A., Rusavskaya, T.N., D'yachkov, A.I. et al. Unsaturated hydantoin derivatives. 18. Alkaline hydrolysis of 2-thioxo-5-arylidenehydantoins and some of their derivatives. Chem Heterocycl Compd 15, 336–341 (1979). https://doi.org/10.1007/BF00474105
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DOI: https://doi.org/10.1007/BF00474105