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Synthesis of Addition Poly(5-methyl-2-norbornene) in the Presence of Palladium Complexes Containing Acyclic Diaminocarbene Ligands

  • Organic Synthesis and Industrial Organic Chemistry
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Abstract

Addition polymerization of a norbornene derivative in the presence of palladium complexes containing acyclic diaminocarbene ligands was studied. Using the polymerization of 5-methyl-2-norbornene as an example, it was shown that such complexes at activation with an organoborate (Na+[B(3,5-(CF3)2C6H5)4]–) catalyze addition polymerization, thereby enabling synthesis of high-molecular-weight products with a unimodal molecular weight distribution. Analysis of the structure of the resulting polymer by 1H NMR spectroscopy made it possible to establish that the polymerization proceeds selectively, without destruction of the bicyclic norbornane fragment. The synthesized addition poly(5-methyl-2-norbornene) was characterized by differential scanning calorimetry, thermogravimetric analysis, and WAXD analysis.

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Funding

This work was supported by a grant from the President of the Russian Federation MD-497.2022.1.3 (agreement no. 075-15-2022-359 от 05.05.22).

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Authors and Affiliations

  1. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, 119991, Moscow, Russia

    A. P. Khrychikova, E. I. Medentseva, E. V. Bermesheva, A. I. Woznyak & M. V. Bermeshev

  2. Mendeleev University of Chemical Technology of Russia, 125047, Moscow, Russia

    A. P. Khrychikova

  3. St. Petersburg State University, 199034, St. Petersburg, Russia

    M. V. Kashina & M. A. Kinzhalov

Authors
  1. A. P. Khrychikova
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  2. E. I. Medentseva
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  3. E. V. Bermesheva
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  4. A. I. Woznyak
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  5. M. V. Kashina
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  6. M. A. Kinzhalov
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  7. M. V. Bermeshev
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Contributions

A.P. Khrychikova, E.I. Medentseva, and E.V. Bermesheva developed a method of addition polymerization and conducted studies on addition polymerization of 5-methyl-2-norbornene, and also studied the properties of the resulting polymer; A.I. Wozniak synthesized the starting monomer (5-methyl-2-norbornene); M.V. Kashina and M.A. Kinzhalov synthesized Pd-complexes with acyclic diaminocarbene ligands required for research; M.V. Bermeshev participated in the interpretation of the obtained results and made the main contribution to writing the text of the manuscript.

Corresponding author

Correspondence to M. V. Bermeshev.

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Additional information

Translated from Zhurnal Prikladnoi Khimii, No. 10, pp. 1312–1319, October, 2022 https://doi.org/10.31857/S0044461822100103

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Khrychikova, A.P., Medentseva, E.I., Bermesheva, E.V. et al. Synthesis of Addition Poly(5-methyl-2-norbornene) in the Presence of Palladium Complexes Containing Acyclic Diaminocarbene Ligands. Russ J Appl Chem 95, 1603–1610 (2022). https://doi.org/10.1134/S1070427222100111

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  • DOI: https://doi.org/10.1134/S1070427222100111

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