Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
1, 3-Dipole in Sulfilimine-Phosphine System. IV. Preparations of Acid Anhydride, Amide, Ester and Thioester
大饗 茂相田 哲夫古川 尚道
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1975 年 23 巻 11 号 p. 3011-3016

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Complexes formed between N-arylsulfonylsulfilimines and triphenylphosphine, for example a couple of S, S-benzyl phenyl p-tosylsulfilimine and triphenylphosphine we call it SP-system for simplicity, were found to react with such compounds as carboxylic acids, alcohols, amines and acid anhydrides affording various interesting products. Among them, the reaction with carboxylic acids gave the corresponding anhydrides in substantial yields, and this reaction can be extended to prepare esters and amides. All these reactions can be explained by assuming the initial formation of a 1, 3-dipole intermediate (sulfurane) between sulfilimine and triphenylphosphine.
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© The Pharmaceutical Society of Japan
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