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Abstract <p>In this work, tri- and tetrahalogen derivatives of 2(5<i>H</i>)-furanone were synthesized and the regioselectivity of their reactions with sulfur-containing nucleophiles was studied. It was shown that reactions of furanones possessing halogen atoms at the vinylic and saturated carbon atoms with 4-methylthiophenol and 2-mercaptoethanol in the presence of Et<sub>3</sub>N proceed regiospecifically with the formation of nucleophilic substitution products at the vinylic carbon atom C<sup>4</sup> of the lactone ring. Using ethane-1,2-dithiol, novel bis-thioethers of furanone and a sulfur fused bicycle of the 2,3-dihydro[1,4]dithiino[2,3-<i>c</i>]furan-5(7<i>H</i>)-one series were obtained.</p>

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Regioselectivity in the Thiylation Reactions of Tri- and Tetrahalogen 2(5H)-Furanone Derivatives

  • 期刊论文

  • 发表日期：

    2025年6月1日

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  • A. M. Khabibrakhmanova,
  • E. G. Bilalova,
  • L. T. Hoang,
  • O. A. Lodochnikova,
  • E. S. Rabbanieva,
  • L. Z. Latypova,
  • A. R. Kurbangalieva

摘要

Abstract

In this work, tri- and tetrahalogen derivatives of 2(5H)-furanone were synthesized and the regioselectivity of their reactions with sulfur-containing nucleophiles was studied. It was shown that reactions of furanones possessing halogen atoms at the vinylic and saturated carbon atoms with 4-methylthiophenol and 2-mercaptoethanol in the presence of Et3N proceed regiospecifically with the formation of nucleophilic substitution products at the vinylic carbon atom C4 of the lactone ring. Using ethane-1,2-dithiol, novel bis-thioethers of furanone and a sulfur fused bicycle of the 2,3-dihydro[1,4]dithiino[2,3-c]furan-5(7H)-one series were obtained.