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2-Imino-6,7,8-trihydroacenaphthylen-1-amine: synthesis and reduction with sodium

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Abstract

The hydrolysis of the tetrasodium salt of dpp-bian (dpp-bian is 1,2-bis[(2,6-diisopropylphenyl)imino]acenaphthene) affords the organic compound 1,6,7,8-H4-dpp-bian (1). This reaction is accompanied by the protonation of the nitrogen atom of the diimine moiety and one ring of the naphthalene system of the molecule. The reduction of 1 with one equivalent or an excess of sodium metal in 1,2-dimethoxyethane gives the salts [(6,7,8-H3-dpp-bian)Na(dme)2] (2a) and [(5,6,7,8-H4-dpp-bian)Na2(dme)2] (3), respectively. The exchange reaction of compound 1 with one equivalent of sodium amide in diethyl ether affords the monosodium salt [(6,7,8-H3-dpp-bian)Na(Et2O)2] (2b). Compounds 1–3 were characterized by NMR and IR spectroscopy and elemental analysis. The molecular structures of 1–3 were determined by X-ray diffraction.

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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

    D. A. Lukina, A. A. Skatova, A. N. Lukoyanov, E. V. Baranov & I. L. Fedushkin

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  1. D. A. Lukina
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  2. A. A. Skatova
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  3. A. N. Lukoyanov
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  4. E. V. Baranov
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  5. I. L. Fedushkin
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Corresponding author

Correspondence to A. A. Skatova.

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Dedicated to Academician of the Russian Academy of Sciences V. N. Charushin on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 908–915, May, 2021.

The study was performed within the framework of the state assignment using equipment of the Joint Analytical Center of the G. A. Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences.

No human or animal subjects were involved in this research.

The authors declare no conflict of interest, financial or otherwise.

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Lukina, D.A., Skatova, A.A., Lukoyanov, A.N. et al. 2-Imino-6,7,8-trihydroacenaphthylen-1-amine: synthesis and reduction with sodium. Russ Chem Bull 70, 908–915 (2021). https://doi.org/10.1007/s11172-021-3166-7

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  • DOI: https://doi.org/10.1007/s11172-021-3166-7

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