Russian Journal of Organic Chemistry

, Volume 54, Issue 8, pp 1228–1231 | Cite as

Alkylation of 2-Sulfanylbenzoxazole with α-Iodoketones in the Absence of Bases

  • L. G. Shagun
  • I. A. Dorofeev
  • L. V. ZhilitskayaEmail author
  • N. O. Yarosh
  • L. I. Larina


Reaction of 2-sulfanylbenzoxazole with 1-iodopropan-2-one, 2-iodo-1-phenylethanone, and 2-iodo-1-(thiophen-2-yl)ethanone without solvent and bases afforded bis(benzoxazol-2-yl)disulfonium derivatives in a single preparative stage. The reaction proceeds as a domino-process and includes the alkylation of a sulfanyl group of benzoxazole, the reduction of iodoketone with hydrogen iodide, the oxidation of 2-sulfanylbenzoxazole to disulfide, the alkylation of disulfide atoms of sulfur, and the formation of triiodideanions. The yield of disulfonium derivatives increases twice in the presence of equimolar amount of iodine.


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Copyright information

© Pleiades Publishing, Ltd. 2018

Authors and Affiliations

  • L. G. Shagun
    • 1
  • I. A. Dorofeev
    • 1
  • L. V. Zhilitskaya
    • 1
    Email author
  • N. O. Yarosh
  • L. I. Larina
    • 1
  1. 1.Favorskii Irkutsk Institute of ChemistrySiberian Branch of Russian Academy of ScienceIrkutsk.Russia

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