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Migratory insertion of bis(diethylamino)phosphine group into the N–N bond in the reaction of substituted hydrazobenzene with (Et2N)2PCl

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Abstract

Oxidative dehydrogenation of 2-bromo-4-methylaniline with manganese(iv) oxide leads to the formation of (E)-1,2-bis(2-bromo-4-methylphenyl)diazene (1). The reaction of 1 with hydrazine hydrate gives the reduction product, 1,2-bis(2-bromo-4-methylphenyl)hydrazine (2). Compound 2 sequentially treated with methyllithium and two equivalents of (Et2N)2PCl in diethyl ether is converted to the diazadiphosphinine derivative. The reaction includes the following steps: 1) the phosphorylation of the nitrogen atom in the dilithium salt of hydrazo derivative 2, 2) the migratory insertion of (Et2N)2P group into the N–N bond, 3) phosphorylation of the second nitrogen atom, 4) arylation of the phosphorus in the (Et2N)2P group.

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Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603950, Nizhny Novgorod, Russian Federation

    Yu. S. Panova, A. V. Sheyanova, E. V. Baranov & A. N. Kornev

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  1. Yu. S. Panova
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  2. A. V. Sheyanova
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  3. E. V. Baranov
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  4. A. N. Kornev
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Correspondence to Yu. S. Panova.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 0132–0138, January, 2020.

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Panova, Y.S., Sheyanova, A.V., Baranov, E.V. et al. Migratory insertion of bis(diethylamino)phosphine group into the N–N bond in the reaction of substituted hydrazobenzene with (Et2N)2PCl. Russ Chem Bull 69, 132–138 (2020). https://doi.org/10.1007/s11172-020-2734-6

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  • DOI: https://doi.org/10.1007/s11172-020-2734-6

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