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Transformations of diphenyl sulfide and diphenylamine on aluminum chloride

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Abstract

Thianthrene has been synthesized by reacting diphenyl sulfide with AlCl3 in heptane at 98°C for 8 h at a diphenyl sulfide: AlCl3 molar ratio of 2: 1; the thianthrene yield is 58%. The reaction mechanism proposed previously has been confirmed by quantum-chemical calculations; the reaction is characterized by a low negative value of Gibbs free energy, a low heat of reaction, and a high activation energy of the first step. Diphenyl ether and diphenylamine do not enter the test reaction because of low nucleophilicity of the heteroatoms; diphenylamine dimerizes under the reaction conditions to form N,N′-diphenylbenzidine.

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Authors and Affiliations

  1. Surgut State University, Surgut, Tyumen oblast, Russia

    V. P. Nekhoroshev, R. R. Gubaidullin & O. I. Tarasova

  2. Tomsk State Pedagogical University, Tomsk, Russia

    A. G. Yarkova

  3. Yugra State University, Khanty-Mansiisk, Tyumen oblast, Russia

    A. V. Nekhorosheva

  4. Faculty of Chemistry, Moscow State University, Moscow, Russia

    I. E. Nifant’ev

  5. Dnepropetrovsk National University of Railway Transport, Dnepr, Russia

    E. O. Voronkov

  6. National Research Tomsk Polytechnic University, Tomsk, Russia

    O. Kh. Poleshchuk

Authors
  1. V. P. Nekhoroshev
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  2. R. R. Gubaidullin
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  3. A. G. Yarkova
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  4. A. V. Nekhorosheva
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  5. I. E. Nifant’ev
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  6. E. O. Voronkov
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  7. O. Kh. Poleshchuk
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  8. O. I. Tarasova
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Corresponding author

Correspondence to V. P. Nekhoroshev.

Additional information

Original Russian Text © V.P. Nekhoroshev, R.R. Gubaidullin, A.G. Yarkova, A.V. Nekhorosheva, I.E. Nifant’ev, E.O. Voronkov, O.Kh. Poleshchuk, O.I. Tarasova, 2017, published in Neftekhimiya, 2017, Vol. 57, No. 2, pp. 214–219.

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Nekhoroshev, V.P., Gubaidullin, R.R., Yarkova, A.G. et al. Transformations of diphenyl sulfide and diphenylamine on aluminum chloride. Pet. Chem. 57, 272–277 (2017). https://doi.org/10.1134/S0965544117020207

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  • DOI: https://doi.org/10.1134/S0965544117020207

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