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Communication | Special issue | Vol 30, No. 1, 1990, pp.367-373
Published online, 1st January, 1970
DOI: 10.3987/COM-89-S71
N3-(Arylthio-, Aralkylthio- and Alkylthio)-5,5-dimethylhydantoins: Sulfenyl Group Transfer Reactions and Their Propertied

Ken’ichi Takeda* and Kusuo Horiki

*Shionogi Research Laboratories, Shionogi & Co. Ltd., Fukushima-ku, Osaka 553-0002, Japan

Abstract

Sulfenyl-transfer reactions toward a variety of nucleophiles were successfully carried out using N3-sulfenyl-substituted 5,5-dimethylhydanations (2a-c). During the course of the synthesis of 2 by the reaction of N1-bromo-5,5-dimethylhydantoin (1c) with disulfides, the sulfenyl groups were found to be at the position of N3 although the bromine was at N1 in the starting monobromohydantoin (1c). Some mechanistic speculations were considerd for the formation of 2 and 1c.