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
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).
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).
P. P. Chapala, M. V. Bermeshev, and N. N. Gavrilova, Polym. Sci., Ser. A 59, 143 (2017).
E. V. Bermesheva, D. A. Alentiev, A. P. Moskalets, and M. V. Bermeshev, Polym. Sci., Ser. B 61(3), 314 (2019).
M. V. Bermeshev and P. P. Chapala, Prog. Polym. Sci. 84, 1 (2018).
Olefin Metathesis and Metathesis Polymerization, Ed. by K. J. Ivin and J. C. Mol (Acad. Press, San Diego, 1997).
N. G. Gaylord, A. B. Deshpande, B. M. Mandal, and M. Martan, J. Macromol. Sci, Chem. 11, 1053 (1977).
N. Balciog`lu and N. Tunog`lu, J. Polym. Sci., Part A: Polym. Chem. 34, 2311 (1996).
M. V. Bermeshev, B. A. Bulgakov, A. M. Genaev, J. V. Kostina, G. N. Bondarenko, and E. S. Finkelshtein, Macromolecules 47, 5470 (2014).
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.
K. Müller, Y. Jung, D. Y. Yoon, S. Agarwal, and A. Greiner, Macromol. Chem. Phys. 211, 1595 (2010).
D. Hermeling and H. J. Schäfer, Chem. Ber. 121, 1151 (1988).
S. D. Tsai and R. A. Register, Macromol. Chem. Phys. 219, 1800059 (2018).
V. A. Petrov and N. V. Vasil’ev, Curr. Org. Synth. 3, 215 (2006).
M. Bermeshev, P. Chapala, V. Lakhtin, A. Genaev, M. Filatova, A. Peregudov, K. Utegenov, N. Ustynyuk, and E. Finkelshtein, Silicon 7, 117 (2015).
H. G. Kuivila and C. R. Warner, Org. Chem. 29, 2845 (1964).
M. Stosur and T. Szymańska-Buzar, J. Mol. Catal. A 286, 98 (2008).
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).
H. Tetsuka, K. Isobe, and M. Hagiwara, Polym. J. 41, 643 (2009).
H. Tetsuka, M. Hagiwara, and S. Kaita, Polym. J. 43, 97 (2011).
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).
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The study was supported by the Russian Science Foundation (project 18-13-00415).
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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