New Synthetic Route for the Preparation of 4-Phenylthio-4-butanolide Derivatives by the Use of the Pummerer Rearrangement

M Watanabe, S Nakamori, H Hasegawa…

文献索引：Watanabe, Mikio; Nakamori, Seijin; Hasegawa, Hatsue; Shirai, Kozo; Kumamoto, Takanobu Bulletin of the Chemical Society of Japan, 1981 , vol. 54, # 3 p. 817 - 821

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被引用次数: 21

摘要

The Pummerer rearrangement reaction of 2-or 3-substituted 4-(phenylsulfinyl) butyric acids in the presence of an excess amount of acetic anhydride and a catalytic amount of p- toluenesulfonic acid in refluxing toluene for 1 h afforded 2-or 3-substituted 4-phenylthio-4- butanolide (17a–f). Thermolysis in pyridine of 4-phenylsulfinyl 4-butanolides, which were prepared by oxidation of 17a–f, afforded 2-or 3-substituted 2-or 3-buten-4-olides.