13012-62-9Relevant academic research and scientific papers
New Synthetic Route for the Preparation of 4-Phenylthio-4-butanolide Derivatives by the Use of the Pummerer Rearrangement
Watanabe, Mikio,Nakamori, Seijin,Hasegawa, Hatsue,Shirai, Kozo,Kumamoto, Takanobu
, p. 817 - 821 (2007/10/02)
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.
Stereochemistry of Free-Radical Eliminations on β-Phenylsulfonyl Radicals
Boothe, Thomas E.,Greene, Joseph L.,Shevlin, Philip B.
, p. 794 - 797 (2007/10/02)
Tributyltin radicals have been allowed to react with erythro- and threo-2-bromo-3-(phenylsulfonyl)butane (5a,b) to generate β-(phenylsulfonyl)-sec-butyl radicals 9.The intermediate 9 eliminates phenylsulfonyl radicals to form 2-butenes in a nonstereospecific manner.The lack of stereospecificity is due to rotation about the C2-C3 bond before the loss of the phenylsulfonyl radical can occur and implies that the stabilization of the radical by sulfur bridging is negligible.
