Beilstein Journal of Organic Chemistry (Nov 2011)

Synthesis and oxidation of some azole-containing thioethers

  • Andrei S. Potapov,
  • Nina P. Chernova,
  • Vladimir D. Ogorodnikov,
  • Tatiana V. Petrenko,
  • Andrei I. Khlebnikov

DOI
https://doi.org/10.3762/bjoc.7.179
Journal volume & issue
Vol. 7, no. 1
pp. 1526 – 1532

Abstract

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Pyrazole and benzotriazole-containing thioethers, namely 1,5-bis(3,5-dimethylpyrazol-1-yl)-3-thiapentane, 1,8-bis(3,5-dimethylpyrazol-1-yl)-3,6-dithiaoctane and 1,3-bis(1,2,3-benzotriazol-1-yl)-2-thiapropane were prepared and fully characterized. Oxidation of the pyrazole-containing thioether by hydrogen peroxide proceeds selectively to provide a sulfoxide or sulfone, depending on the amount of oxidant used. Oxidation of the benzotriazole derivative by hydrogen peroxide is not selective, and sulfoxide and sulfone form concurrently. Selenium dioxide-catalyzed oxidation of benzotriazole thioether by H2O2, however, proceeds selectively and yields sulfoxide only.

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