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Nitrones and Nitroso Compounds in the Coupling Reactions for the Synthesis of Macromolecular Structures Based on Polystyrene

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Abstract

The capacity of the coupling reactions of polystyrene bearing an ω-terminal bromine group in the presence of various nitrones and nitroso compounds has been disclosed. As exemplified by the coupling using С-phenyl-N-tert-butylnitrone, acetonitrile and tetrahydrofuran have been found the best solvents of the probed series (toluene, ethyl acetate, benzene, acetonitrile, and tetrahydrofuran). The said solvents have revealed the strongest coordination ability towards the catalytical system based on copper(I) bromide and have afforded high coupling degree (above 90%) preserving low polydispersity of the synthesized samples. It has been shown that the nitroso compounds involved in the coupling with styrene favor the formation of terminal nitroxyl fragments. In contrast to nitroso compounds, the nitrones have afforded symmetrical high-molecular alkoxyamines bearing a nitroxyl fragment in the middle of the polymer chain.

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ACKNOWLEDGMENTS

Authors are grateful to I.A. Kirilyuk and I.F. Zhurko (Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, RAS) for the provided nitrones (BMPO, DIO, and DIOO).

Funding

This study was financially supported by the Russian Foundation for Basic Research (project code 20-03-00150).

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Authors and Affiliations

  1. Lobachevsky State University of Nizhny Novgorod, 603950, Nizhny Novgorod, Russia

    E. V. Kolyakina, F. Kh. Shoipova & D. F. Grishin

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  1. E. V. Kolyakina
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  2. F. Kh. Shoipova
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  3. D. F. Grishin
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Correspondence to D. F. Grishin.

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Translated by E. Karpushkin

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Kolyakina, E.V., Shoipova, F.K. & Grishin, D.F. Nitrones and Nitroso Compounds in the Coupling Reactions for the Synthesis of Macromolecular Structures Based on Polystyrene. Polym. Sci. Ser. B 64, 359–372 (2022). https://doi.org/10.1134/S1560090422700257

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