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Synthesis, structure, and properties of the product formed in the reaction of ortho-diphenylphosphinobenzaldehyde and N-tosyl-1,2-phenylenediamine

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Abstract

Interaction of ortho-diphenylphosphinobenzaldehyde with N-tosyl-1,2-phenylenediamine afforded the product of intramolecular Wittig reaction, N-{2-[2-(Diphenylphosphoryl)benzylamino]phenyl}-4-methylbenzenesulfonamide. Its structure was established on the basis of IR, 1H NMR, 13C NMR, and 2D 1H NMR (COSY) spectroscopy. Reaction mechanism was studied by means of quantum chemistry DFT method. Complexforming property of the obtained diphenylphosphine oxide was investigated.

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Correspondence to L. D. Popov.

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Original Russian Text © L.D. Popov, S.A. Borodkin, M.E. Kletskii, O.N. Burov, P.G. Morozov, I.N. Shcherbakov, Yu.P. Tupolova, L.I. Etmetchenko, A.V. Tkachuk, V.A. Kogan, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 1, pp. 112–118.

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Popov, L.D., Borodkin, S.A., Kletskii, M.E. et al. Synthesis, structure, and properties of the product formed in the reaction of ortho-diphenylphosphinobenzaldehyde and N-tosyl-1,2-phenylenediamine. Russ J Gen Chem 85, 104–110 (2015). https://doi.org/10.1134/S1070363215010181

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