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Synthesis and structures of 4,5-dimethyl-1,3-bis(pyridin-2-ylmethyl)-1H-imidazolium chloride and 1,1′-bis(pyridin-2-ylmethyl)-2,2′-bis(4,5-dimethylimidazole)

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Abstract

4,5-Dimethyl-1,3-bis(pyridin-2-ylmethyl)-1H-imidazolium chloride (1) was synthesized and characterized by IR and NMR spectroscopy and X-ray diffraction. An attempt to prepare the free tridentate N-heterocyclic carbene pincer ligand by the reaction of 1 with KN(SiMe3)2 resulted in the formation of 1,1′-bis(pyridin-2-ylmethyl)-2,2′-bis(4,5-dimethylimidazole) as a product of dimerization of the target carbene followed by the rearrangement accompanied by the elimination of dipyridylethane.

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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

    I. V. Lapshin, A. V. Cherkasov & A. A. Trifonov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119334, Moscow, Russian Federation

    A. A. Trifonov

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  1. I. V. Lapshin
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  2. A. V. Cherkasov
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  3. A. A. Trifonov
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Correspondence to A. A. Trifonov.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1957–1963, October, 2021.

This study was financially supported by the Russian Foundation for Basic Research (Project No. 19-33-90273). The X-ray diffraction and NMR spectroscopic studies of compounds 1 and 2 were performed using equipment of the Joint Analytical Center of the G. A. Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences with the financial support by the Ministry of Science and Higher Education of the Russian Federation (Grant “Promotion of the Development of Infractructure of Centers for Shared Use of Scientific Equipment,” agreement number 13.CKP.21.0017).

This paper does not contain descriptions of studies on animals or humans.

The authors declare no competing interests.

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Lapshin, I.V., Cherkasov, A.V. & Trifonov, A.A. Synthesis and structures of 4,5-dimethyl-1,3-bis(pyridin-2-ylmethyl)-1H-imidazolium chloride and 1,1′-bis(pyridin-2-ylmethyl)-2,2′-bis(4,5-dimethylimidazole). Russ Chem Bull 70, 1957–1963 (2021). https://doi.org/10.1007/s11172-021-3303-3

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