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Beilstein-Institut, Beilstein Journal of Organic Chemistry, (7), p. 1526-1532, 2011

DOI: 10.3762/bjoc.7.179

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Synthesis and oxidation of some azole-containing thioethers

Journal article published in 2011 by Andrei S. Potapov, Nina P. Chernova, Vladimir D. Ogorodnikov, Tatiana V. Petrenko, Andrei I. Khlebnikov ORCID
This paper is made freely available by the publisher.
This paper is made freely available by the publisher.

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Abstract

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.