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Synthesis of dicationic hetarylmethylimidazolium salts via the reaction of N, N′-diaryl-4-chloromethylimidazolium chlorides with N-heterocycles

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Abstract

The reaction between N, N′-diaryl-4-chloromethylimidazolium chlorides and N-nucleophiles, viz. various azoles and azines, which proceeds via nucleophilic substitution of the chlorine atom in the chloromethyl group and leads to new dicationic 4-hetarylmethylimidazolium salts, was investigated. This reaction is reversible, whereas the yield of product of the nucleophilic substitution depends significantly on the structure of heterocyclic nucleophile and the nature of used solvent. A series of new dicationic 4-hetarylmethylimidazolium salts was obtained, and they are of interest as promising components of ionic liquids and precursors of N-heterocyclic carbenes.

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Authors and Affiliations

  1. Platov South-Russian State Polytechnic University (NPI), 132 ul. Prosveshcheniya, 346428, Novocherkassk, Rostov region, Russian Federation

    M. A. Shevchenko, D. V. Pasyukov, Yu. N. Tkachenko & V. M. Chernyshev

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    M. E. Minyaev

Authors
  1. M. A. Shevchenko
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  2. D. V. Pasyukov
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  3. Yu. N. Tkachenko
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  4. M. E. Minyaev
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  5. V. M. Chernyshev
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Corresponding author

Correspondence to V. M. Chernyshev.

Additional information

The authors are grateful to Academician of the Russian Academy of Sciences V. P. Ananikov for a fruitful discussion of the results reported herein and valuable comments.

This work was financially supported by the Russian Science Foundation (Project No. 22-23-00304).

No human or animal subjects were used in this research.

The authors declare no competing interests.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 5, pp. 1225–1232, May, 2023.

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Shevchenko, M.A., Pasyukov, D.V., Tkachenko, Y.N. et al. Synthesis of dicationic hetarylmethylimidazolium salts via the reaction of N, N′-diaryl-4-chloromethylimidazolium chlorides with N-heterocycles. Russ Chem Bull 72, 1225–1232 (2023). https://doi.org/10.1007/s11172-023-3893-z

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  • DOI: https://doi.org/10.1007/s11172-023-3893-z

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