ONE-POT SYNTHESIS OF NORBORNENE-CYCLOOCTENE COPOLYMERS

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Abstract

The one-pot synthesis of random multiblock copolymers of norbornene and cyclooctene has been performed for the first time. It is shown that the first generation Grubbs Ru-carbene complex makes it possible to obtain these copolymers directly from monomers. In the course of one-pot synthesis, the metathesis polymerization of norbornene, which has a markedly higher ring strain, occurs first. Then, cyclooctene polymerizes and simultaneously an interchain cross-metathesis reaction takes place, during which the block structure of the copolymer is formed. Compared to the previously studied interaction of polynorbornene and polycyclooctene, the one-pot method makes it possible to obtain copolymers with a higher molar mass at a lower catalyst consumption.

About the authors

M. L. Gringolts

Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Email: yar@ips.ac.ru
Russian, 119991, Moscow

A. S. Marchenko

Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Email: yar@ips.ac.ru
Russian, 119991, Moscow

A. S. Peregudov

Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: yar@ips.ac.ru
Russian, 119991, Moscow

Yu. I. Denisova

Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Email: yar@ips.ac.ru
Russian, 119991, Moscow

Y. V. Kudryavtsev

Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences

Author for correspondence.
Email: yar@ips.ac.ru
Russian, 119991, Moscow

References

  1. Norsorex (интернет). Доступно по: https://www.norsorex.com/. Ссылка активна на 29 декабря 2022 г.
  2. Vestenamer (интернет). Доступно по: https://www.vestenamer.com/en. Ссылка активна на 29 декабря 2022 г.
  3. Leimgruber S., Trimmel G. // Monatsh. Chem. 2015. V. 146. P. 1081–1097. https://doi.org/10.1007/s00706-015-1501-0
  4. Flid V.R., Gringolts M.L., Shamsiev R.S., Finkel-shtein E.Sh. // Russ. Chem. Rev. 2018. V. 87. № 12. P. 1169–1205. https://doi.org/10.1070/RCR4834
  5. Zubkevich S.V., Tuskaev V.A., Gagieva S.Ch., Buly-chev B.M. // Russ. Chem. Rev. 2022. V. 91. № 3. RCR5021. https://doi.org/10.1070/RCR5021
  6. Nazarov I.V., Bermesheva E.V., Potapov K.V., Khesina Z.B., Il’in M.M., Melnikova E.K., Bermeshev M.V. // Mendeleev Commun. 2021. V. 31. № 5. P. 690–692. https://doi.org/10.1016/j.mencom.2021.09.032
  7. Ivin K.J., Mol. J.C. Olefin metathesis and metathesis polymerization. London: Academic Press, 1997. P. 472.
  8. Schleyer P.v.R., Williams J.E., Blanchard K.R. // J. Am. Chem. Soc. 1970. V. 92. P. 2377–2386. https://doi.org/10.1021/ja00711a030
  9. Bornand M., Chen P. // Angew. Chem., Int. Ed. 2005. V. 44. P. 7909–7911. https://doi.org/10.1002/anie.200502606
  10. Walker R., Conrad R.M., Grubbs R.H. // Macromolecules. 2009. V. 42. № 3. P. 599–605. https://doi.org/10.1021/ma801693q
  11. Kohara T. // Macromol. Symp. 1996. V. 101. P. 571–579. https://doi.org/10.1002/masy.19961010163
  12. Dragutan V., Streck R. Catalytic polymerization of cycloolefins: Ionic, Ziegler-Natta and ring-opening metathesis polymerization. Amsterdam: Elsevier, 2000. V. 131. P. 1292.
  13. Nunes P.S., Ohlsson P.D., Ordeig O., Kutter J.P. // Microfluid. Nanofluid. 2010. V. 9. P. 145–161. https://doi.org/10.1007/s10404-010-0605-4
  14. Yamazaki M. // J. Mol. Catal. A: Chem. 2004. V. 213. № 1. P. 81–87. https://doi.org/10.1016/j.molcata.2003.10.058
  15. Naga N., Kikuch G., Toyota A. // Polymer. 2006. V. 47. P. 6081–6090. https://doi.org/10.1016/j.polymer.2006.06.015
  16. Chaimongkolkunasin S., Hou X., Nomura K. // J. Polym. Sci., Part A: Polym. Chem. 2017. V. 55. P. 3067–3074. https://doi.org/10.1002/pola.28622
  17. Kong Y., Xu Sh., Song H., Wang B. // Organometallics. 2012. V. 31. № 15. P. 5527–5532. https://doi.org/10.1021/om300474n
  18. Li M., Song H., Wang B. // Eur. J. Inorg. Chem. 2015. P. 4055–4061. https://doi.org/10.1002/ejic.201500499
  19. Bornand M., Torker S., Chen P. // Organometallics. 2007. V. 26. P. 3585–3596. https://doi.org/10.1021/om700321a
  20. Torker S., Müller A., Sigrist R., Chen P. // Organometallics. 2010. V. 29. P. 2735–2751. https://doi.org/10.1021/om100185g
  21. Torker S., Müller A., Chen P. // Angew. Chem. 2010. V. 122. P. 3850–3854. https://doi.org/10.1002/ange.200906846
  22. Vehlow K., Wang D., Buchmeiser M.R., Blechert S. // Angew. Chem. Int. Ed. 2008. V. 47. P. 2615–2618. https://doi.org/10.1002/anie.200704822
  23. Lichtenheldt M., Wang D., Vehlow K., Reinhardt I., Kühnel C., Decker U., Blechert S., Buchmeiser M.R. // Chem. Eur. J. 2009. V. 15. P. 9451–9457. https://doi.org/10.1002/chem.200900384
  24. Buchmeiser M.R., Ahmad I., Gurram V., Kumar P.S. // Macromolecules. 2011. V. 44. № 11. P. 4098–4106. https://doi.org/10.1021/ma200995m
  25. Gringolts M.L., Denisova Y.I., Shandryuk G.A., Kren-tsel L.B., Litmanovich A.D., Finkelshtein E.S., Kudryavtsev Y.V. // RSC Adv. 2015. V. 5. № 1. P. 316–319. https://doi.org/10.1039/C4RA12001A
  26. Denisova Y.I., Gringolts M.L., Peregudov A.S., Krentsel L.B., Litmanovich E.A., Litmanovich A.D., Finkelshtein E.S., Kudryavtsev Y.V. // Beilstein J. Org. Chem. 2015. V. 11. P. 1796–1808. https://doi.org/10.3762/bjoc.11.195
  27. Shandryuk G.A., Denisova Y.I., Gringolts M.L., Kren-tsel L.B., Litmanovich A.D., Finkelshtein E.S., Kudryavtsev Y.V. // Eur. Polym. J. 2017. V. 86. P. 143–153. https://doi.org/10.1016/j.eurpolymj.2016.11.025
  28. Gringolts M.L., Denisova Y.I., Finkelshtein E.Sh., Kudryavtsev Y.V. // Beilstein J. Org. Chem. 2019. V. 15. P. 218–235. https://doi.org/10.3762/bjoc.15.21
  29. Morontsev A.A., Denisova Y.I., Gringolts M.L., Filato-va M.P., Shandryuk G.A., Finkelshtein E.S., Kudryav-tsev Y.V. // Polym. Sci., Ser. B. 2018. V. 60. № 5. P. 688–698. https://doi.org/10.1134/S1560090418050111

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Copyright (c) 2023 М.Л. Грингольц, А.С. Марченко, А.С. Перегудов, Ю.И. Денисова, Я.В. Кудрявцев

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