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Paper | Regular issue | Vol 96, No. 2, 2018, pp.254-272
Published online, 19th January, 2018
DOI: 10.3987/COM-17-13853
■ Syntheses of 4-Acetoxy- or Acetylthio-2-substituted Tetrahydrothiophene

Yaxi Li, Rui Ding, Yongguo Liu, Bianbian Ma, Baoguo Sun, and Hongyu Tian*

*Beijing Advanced Innovation Center for Food Nutrition and Human Health, Beijing Key Laboratory of Flavor Chemistry, Beijing Technology and Business University, Fucheng Road 11#, Haidian District 100048, China

Abstract

The generality of a three-step route for the preparation of 4-acetoxy-2-alkyltetrahydrothiophenes was investigated, which started from 1-alken-4-ols including epoxidation, mesylation and intramolecular nucleophilic substitution. 4-Acetoxy-2-alkyltetrahydrothiophenes could be produced in moderate to good yields by this method, even a bulky substituted group on the C-4 position of 1-alken-4-ol did not make significant effect on the reaction. In contrast, 1-alken-4-ols with an aryl group attached to the C-4 position gave acyclic products 1,4-diacetylthio-4-arylbutan-2-yl acetates when the reactions were carried out in acetonitrile under reflux. Whereas, 4-acetylthio-2-aryltetrahydrothiophenes were obtained in good yields when the reactions were carried out in toluene under reflux. A possible pathway for the latter involving an intermediate of episulfide was proposed.