78429-05-7

Upstream product

• 78428-85-0 2-(1-Phenyl-2-phenylsulfanyl-ethyl)-malonic acid diethyl ester 
• 54681-09-3 1-bromo-1-phenyl-2-phenylthioethane 
• 67210-34-8 1-phenyl-2-phenylsulfanyl-ethanol 
• 16222-10-9 1-phenyl-2-(phenylthio)ethanone 
• 16619-62-8 (2-(phenylsulfinyl)vinyl)benzene 
• 78428-91-8 3-phenyl-4-(phenylthio)butyric acid 

Downstream Products

• 78428-97-4 3-phenyl-4-phenylthio-4-butenolide 
• 78429-12-6 5-Benzenesulfinyl-4-phenyl-dihydro-furan-2-one 
• 1575-47-9 4-phenyl-5H-furan-2-one 

Relevant academic research and scientific papers

Diastereoselectivity in the Preparation of 4-Phenylthio-4-butanolide Derivatives by the Use of the Pummerer Rearrangement

Diastereoselectivity in the preparation of 4-phenylthio-4-butanolide derivatives by the Pummerer rearrangement of 4-phenylsulfinylbutanoic acid derivatives was clarified.The reaction of 3-alkyl-4-phenylsulfinylbutanoic acid with acetic anhydride resulted in the predominant formation of trans-3-alkyl-4-phenylthio-4-butanolide.Lactonization of 2,3-dialkyl-4-phenylsulfinylbutanoic acid gave (2RS,3RS,4SR)-2,3-dialkyl-4-phenylthio-4-butanolide predominantly.

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

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.