5,5-DiphenylhydantoinのPhenylsulfonyl化反応および3-Phenylsulfonyl-5,5-diphenylhydantoinの転移反応

概要

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Reaction of 1.0 molar equivalent of 5,5-diphenylhydrantoin (I) with 1.0 molar equivalent of phenylsulfonyl chloride (II) in the presence of sodium hydroxide or triethylamine results in the formation of 3-phenylsulfonyl-5,5-diphenylhydrantoin (III), while the use of 2.0 molar equivalent of II gives 1,3-diphenylsulfonyl-5,5-diphenylhydantoin (IV). When pyridine is used as the base, only III is obtained from either 1.0 or 2.0 molar equivalent of II. Heating of III with equimolar amount of sodium hydride in benzene results in rearrangement to from 1-phenylsulfonyl-5,5-diphenylhydantoin (IV). Structure of III, IV, and VI was their from proved infrared, nuclear magnetic resonance spectra, and from their chemical reactions.
公益社団法人日本薬学会の論文
1969-11-25