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Stereoselective synthesis and metathesis polymerization of exo-5-(Pentamethyldisiloxanyl) norbornene

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Abstract

A one-step selective method based on the hydrosilylation of 2,5-norbornadiene with commercially available silanes in the presence of a Pd-catalyst and bulky ligand R-MOP is developed for the synthesis of exo-isomers of silicon-containing norbornenes. This approach leads to the formation of exclusively exo-isomers. The absence of the steps of alkylation with organometallic reagents and photochemical isomerization makes the proposed approach attractive for the targeted design and synthesis of new polymeric materials with the required properties.

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REFERENCES

  1. D. A. Alentiev, E. S. Egorova, M. V. Bermeshev, L. E. Starannikova, M. A. Topchiy, A. F. Asachenko, P. S. Gribanov, M. S. Nechaev, Y. P. Yampolskii, and E. S. Finkelshtein, J. Mater. Chem. A 6, 19393 (2018).

    Article  CAS  Google Scholar 

  2. B. J. Sundell, J. A. Lawrence III, D. J. Harrigan, J. T. Vaughn, T. S. Pilyugina, and D. R. Smith, RSC Adv. 6, 51619 (2016).

  3. P. P. Chapala, M. V. Bermeshev, and N. N. Gavrilova, Polym. Sci., Ser. A 59, 143 (2017).

    Article  CAS  Google Scholar 

  4. E. V. Bermesheva, D. A. Alentiev, A. P. Moskalets, and M. V. Bermeshev, Polym. Sci., Ser. B 61(3), 314 (2019).

  5. M. V. Bermeshev and P. P. Chapala, Prog. Polym. Sci. 84, 1 (2018).

    Article  CAS  Google Scholar 

  6. Olefin Metathesis and Metathesis Polymerization, Ed. by K. J. Ivin and J. C. Mol (Acad. Press, San Diego, 1997).

    Google Scholar 

  7. N. G. Gaylord, A. B. Deshpande, B. M. Mandal, and M. Martan, J. Macromol. Sci, Chem. 11, 1053 (1977).

    Article  Google Scholar 

  8. N. Balciog`lu and N. Tunog`lu, J. Polym. Sci., Part A: Polym. Chem. 34, 2311 (1996).

    Article  Google Scholar 

  9. M. V. Bermeshev, B. A. Bulgakov, A. M. Genaev, J. V. Kostina, G. N. Bondarenko, and E. S. Finkelshtein, Macromolecules 47, 5470 (2014).

    Article  CAS  Google Scholar 

  10. E. Finkelshtein, M. Gringolts, M. Bermeshev, P. Chapala, and Yu. Rogan, “Polynorbornenes,” in Membrane Materials for Gas and Vapor Separation Synthesis and Application of Silicon-Containing Polymers, Ed. by Yu. Yampolskii and E. Finkelshtein (Wiley, Chichester, 2017), p. 143.

    Google Scholar 

  11. K. Müller, Y. Jung, D. Y. Yoon, S. Agarwal, and A. Greiner, Macromol. Chem. Phys. 211, 1595 (2010).

    Article  Google Scholar 

  12. D. Hermeling and H. J. Schäfer, Chem. Ber. 121, 1151 (1988).

    Article  CAS  Google Scholar 

  13. S. D. Tsai and R. A. Register, Macromol. Chem. Phys. 219, 1800059 (2018).

    Article  Google Scholar 

  14. V. A. Petrov and N. V. Vasil’ev, Curr. Org. Synth. 3, 215 (2006).

    Article  CAS  Google Scholar 

  15. M. Bermeshev, P. Chapala, V. Lakhtin, A. Genaev, M. Filatova, A. Peregudov, K. Utegenov, N. Ustynyuk, and E. Finkelshtein, Silicon 7, 117 (2015).

    Article  CAS  Google Scholar 

  16. H. G. Kuivila and C. R. Warner, Org. Chem. 29, 2845 (1964).

    Article  CAS  Google Scholar 

  17. M. Stosur and T. Szymańska-Buzar, J. Mol. Catal. A 286, 98 (2008).

    Article  CAS  Google Scholar 

  18. M. V. Bermeshev, A. V. Syromolotov, L. E. Starannikova, M. L. Gringolts, V. G. Lakhtin, Y. P. Yampolskii, and E. S. Finkelshtein, Macromolecules 46, 8973 (2013).

    Article  CAS  Google Scholar 

  19. H. Tetsuka, K. Isobe, and M. Hagiwara, Polym. J. 41, 643 (2009).

    Article  CAS  Google Scholar 

  20. H. Tetsuka, M. Hagiwara, and S. Kaita, Polym. J. 43, 97 (2011).

    Article  CAS  Google Scholar 

  21. D. A. Alentiev, M. V. Bermeshev, L. E. Starannikova, E. V. Bermesheva, V. P. Shantarovich, V. G. Bekeshev, Y. P. Yampolskii, and E. S. Finkelshtein, J. Polym. Sci., Part A: Polym. Chem. 56, 1234 (2018).

    Article  CAS  Google Scholar 

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Funding

The study was supported by the Russian Science Foundation (project 18-13-00415).

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Correspondence to M. V. Bermeshev.

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Guseva, M.A., Alentiev, D.A., Gavrilov, D.I. et al. Stereoselective synthesis and metathesis polymerization of exo-5-(Pentamethyldisiloxanyl) norbornene. Polym. Sci. Ser. C 61, 102–106 (2019). https://doi.org/10.1134/S1811238219010089

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  • DOI: https://doi.org/10.1134/S1811238219010089

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