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Synthesis and structure of unsymmetrical 1,1′-disubstituted cyclopropane-containing azinylferrocenes

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Abstract

A simple and convenient approach to the synthesis of the derivatives of unsymmetrical 1,1′-disubstituted cyclopropane-containing azinylferrocenes was suggested. A regioselective method for the Friedel—Crafts acylation of monoazinyl-substituted ferrocenes with a 4-chlorobutyryl chloride—AlCl3 mixture in CH2Cl2 under an inert atmosphere was elaborated. The acylation product on treatment with ButOK in DMSO readily underwent γ-elimination of HCl to give the corresponding cyclopropanes. The structures of the synthesized compounds were confirmed by IR spectroscopy, 1H and 13C spectroscopy, mass spectrometry, and X-ray diffraction analysis.

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Funding

This work was financially supported by the Ministry of Science and Higher Education of the Russian Federation in the framework of the Program for Development of the Ural Federal University named after the first President of Russia B. N. Yeltsin in accordance with the Program of Strategic Development of Academic Leadership “Priority 2030”.

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Authors and Affiliations

  1. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Yekaterinburg, Russian Federation

    A. A. Musikhina, I. A. Utepova, E. Yu. Zyryanova, A. K. Terekhova, E. D. Kazakova & O. N. Chupakhin

  2. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22 ul. S. Kovalevskoy, 620219, Yekaterinburg, Russian Federation

    I. A. Utepova, I. N. Ganebnykh, E. D. Kazakova & O. N. Chupakhin

  3. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, 31 Leninsky prosp., 119991, Moscow, Russian Federation

    M. A. Kiskin

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  1. A. A. Musikhina
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  2. I. A. Utepova
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Correspondence to I. A. Utepova or O. N. Chupakhin.

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Based on the materials of the VII International Conference “Modern Synthetic Methodologies for Creating Drugs and Functional Materials” (MOSM 2023) dedicated to the 125th birth anniversary of Academician I. Ya. Postovsky (September 10–16, 2023, Yekaterinburg—Perm, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 12, pp. 2815–2824, December, 2023.

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Musikhina, A.A., Utepova, I.A., Zyryanova, E.Y. et al. Synthesis and structure of unsymmetrical 1,1′-disubstituted cyclopropane-containing azinylferrocenes. Russ Chem Bull 72, 2815–2824 (2023). https://doi.org/10.1007/s11172-023-4090-9

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