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Oxidation of 2-cyanoprop-2-enethioamides with hydrogen peroxide

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Abstract

Oxidation of (E)-3-aryl-2-cyanoprop-2-enethioamides with 32% H2O2 under mild conditions gave (E)-3-aryl-2-cyano-1-iminioprop-2-ene-1-sulfenates in 70–88% yields. Under the conditions of the Radziszewski reaction (H2O2, 10% aqueous KOH) or upon prolonged treatment with H2O2, (E)-3-aryl-2-cyanoprop-2-enethioamides underwent transformations leading to complex mixtures of oxidation products. In some cases, 3-aryloxirane-2,2-dicarboxamides were isolated from those mixtures in low yields (<20%). Treatment of 3-arylamino-2-cyanoprop-2-enethioamides with the system H2O2/KOH in ethanol afforded (arylaminomethylidene)malononitriles.

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Authors and Affiliations

  1. ChemEx Laboratory, V. Dal’East-Ukranian National University, 20a Molodyozhny kv., 91034, Lugansk, Ukraine

    V. V. Dotsenko & S. G. Krivokolysko

  2. State Enterprise “Luganskstandartmetrologiya”, 50 ul. Timiryazeva, 91021, Lugansk, Ukraine

    V. V. Dotsenko

  3. Institute for Single Crystals, National Academy of Sciences of Ukraine, 60 prosp. Lenina, 61178, Kharkov, Ukraine

    S. V. Shishkina & O. V. Shishkin

  4. V. N. Karazin Kharkov National University, 4 pl. Svobody, 61022, Kharkov, Ukraine

    O. V. Shishkin

Authors
  1. V. V. Dotsenko
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  2. S. G. Krivokolysko
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  3. S. V. Shishkina
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  4. O. V. Shishkin
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Correspondence to V. V. Dotsenko.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2065–2070, November, 2012.

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Dotsenko, V.V., Krivokolysko, S.G., Shishkina, S.V. et al. Oxidation of 2-cyanoprop-2-enethioamides with hydrogen peroxide. Russ Chem Bull 61, 2082–2087 (2012). https://doi.org/10.1007/s11172-012-0291-3

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  • DOI: https://doi.org/10.1007/s11172-012-0291-3

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