Transformations of diphenyl sulfide and diphenylamine on aluminum chloride: Fid-Bau Portal

Transformations of diphenyl sulfide and diphenylamine on aluminum chloride

Nekhoroshev, V. P. / Gubaidullin, R. R. / Yarkova, A. G. / Nekhorosheva, A. V. / Nifant’ev, I. E. / Voronkov, E. O. / Poleshchuk, O. Kh. / Tarasova, O. I.

Abstract

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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Transformations of diphenyl sulfide and diphenylamine on aluminum chloride

Nekhoroshev, V. P. / Gubaidullin, R. R. / Yarkova, A. G. / Nekhorosheva, A. V. / Nifant’ev, I. E. / Voronkov, E. O. / Poleshchuk, O. Kh. / Tarasova, O. I.

Abstract

Transformations of diphenyl sulfide and diphenylamine on aluminum chloride

Nekhoroshev, V. P. / Gubaidullin, R. R. / Yarkova, A. G. / Nekhorosheva, A. V. / Nifant’ev, I. E. / Voronkov, E. O. / Poleshchuk, O. Kh. / Tarasova, O. I.