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Reaction of N-chloro-1,4-benzoquinone imines with thiols

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Abstract

N-Chloro-1,4-benzoquinone imines reacted with arenethiols to give different products, depending on the conditions and initial quinone imine structure. N-(Arylsulfanyl)-1,4-benzoquinone imines were obtained as a result of nucleophilic substitution of the chlorine atom, and 1,4-benzoquinone imines containing an aryl-sulfanyl substituent in the quinoid ring were formed according to the radical mechanism. The reactions of N-chloro-1,4-benzoquinone imines with heterocyclic thiols afforded only the corresponding chlorine substitution products.

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Authors and Affiliations

  1. Donbass State Engineering Academy, ul. Shkadinova 72, Kramatorsk, 84313, Ukraine

    S. A. Konovalova, A. P. Avdeenko, A. A. Santalova & E. N. Lysenko

  2. Ukrainian State University of Chemical Technology, pr. Gagarina 8, Dnepropetrovsk, 49005, Ukraine

    K. S. Burmistrov

Authors
  1. S. A. Konovalova
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  2. A. P. Avdeenko
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  3. A. A. Santalova
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  4. E. N. Lysenko
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  5. K. S. Burmistrov
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Correspondence to A. P. Avdeenko.

Additional information

Original Russian Text © S.A. Konovalova, A.P. Avdeenko, A.A. Santalova, E.N. Lysenko, K.S. Burmistrov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 9, pp. 1300–1308.

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Konovalova, S.A., Avdeenko, A.P., Santalova, A.A. et al. Reaction of N-chloro-1,4-benzoquinone imines with thiols. Russ J Org Chem 52, 1287–1296 (2016). https://doi.org/10.1134/S1070428016090062

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  • DOI: https://doi.org/10.1134/S1070428016090062

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