Abstract
This review summarizes the data on the addition polymerization of norbornene catalyzed by various transition metal complexes published over the period of 2008–2018. The interest in the addition polynorbornenes is due to their dielectric, mechanical, and optical properties, which makes them attractive for use in the microelectronic industry and optics. The regularities of polymerization using catalysts based on Ti, Ir, Ni, Pd, and Cu compounds are considered.
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Notes
The term “allyl compounds” in this paper refers not only to compounds containing a simple allyl group (CH2=CH–CH2–) but also to those that contain substituted allyl groups or an allyl group, which is part of a closed cyclic system [77].
The term “naked” is used in relation to metal atoms in complex compounds in which the ligand can be quantitatively substituted by substances involved in catalytic reactions [77].
REFERENCES
K. L. Makovetskii, Vysokomol. Soedin., Ser. A 36, 1712 (1994).
K. L. Makovetskii, Vysokomol. Soedin., Ser. B 41, 1525 (1999).
K. L. Makovetskii, Polym. Sci., Ser. C 50, 22 (2008).
C. Janiak and P. G. Lassahn, Macromol. Rapid Commun. 22, 479 (2001).
C. Janiak and P. G. Lassahn, J. Mol. Catal. A: Chem. 166, 193 (2001).
F. Blank and C. Janiak, Coord. Chem. Rev. 253, 827 (2009).
B. L. Goodall, in Late Transition Metal Polymerization Catalysis, Ed. by B. Rieger, L. Saunders Baugh, S. Kacker, and S. Striegler (Wiley-VCH Verlag GbH, Weinheim, 2003), p. 101.
R. Ma, Y. Hou, J. Gao, and F. Bao, Polym. Rev. 49, 249 (2009).
L. Boggioni and I. Tritto, in Polyolefins: 50 Years After Ziegler and Natta II, Ed. by W. Kaminsky (Spriner-Verlag, Berlin; Heidelberg, 2013), p. 117.
M. V. Bermeshev and P. P. Chapala, Prog. Polym. Sci. 84, 1 (2018).
M. R. Flid, M. L. Gringolts, R. S. Shamsiev, and E. S. Finkelshtein, Russ. Chem. Rev. 87, 1169 (2018).
L. Boggioni and I. Tritto, MRS Bull. 38, 245 (2013).
W. Zhao and K. Nomura, Catalysts 6, 175 (2016).
R. F. Ohm and T. M. Vial, J. Elastomers Plast. 10, 150 (1978).
G. B. Kauffmaan, S. W. Mason, and R. B. Seymour, J. Chem. Educ. 67, 198 (1990).
Sanyo Corporation of America. http://sanyocorp.com/materials/norsorex/rubber. Cited 2019
K. A. Ogawa, A. E. Goetz, and A. J. Boydston, J. Am. Chem. Soc. 137, 1400 (2015).
Olefin Metathesis and Metathesis Polymerization, Ed. by K. J. Ivin and J. C. Mol (Acad. Press, San Diego, 1997).
B. Lebedev, Y. Kiparisova, and K. Makovetsky, Makromol. Chem. 193, 1399 (1992).
N. N. Smirnova and B. V. Lebedev, Polym. Sci., Ser. B 43, 315 (2001).
M. L. Gringolts, M. V. Bermeshev, K. L. Makovetsky, and E. S. Finkelshtein, Eur. Polym. J. 45, 2142 (2009).
C. W. Bielawski and R. H. Grubbs, Prog. Polym. Sci. 32, 1 (2007).
G. C. Vougioukalakis and R. H. Grubbs, Chem. Rev. 110, 1746 (2010).
Handbook of Metathesis, Ed. by R. H. Grubbs, A. G. Wenzel, D. J. O’Leary, and E. Khosravi (Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2015), Vol. 1.
Handbook of Metathesis, Ed. by R. H. Grubbs, A. G. Wenzel, D. J. O’Leary, and E. Khosravi (Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2015), Vol. 2.
Handbook of Metathesis, Ed. by R. H. Grubbs, A. G. Wenzel, D. J. O’Leary, and E. Khosravi (Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2015), Vol. 3.
Handbook of Metathesis, Ed. by R. H. Grubbs (Wiley-VCH, Weinheim, 2003), Vol. 3.
H. Martinez, N. Ren, M. Matta, and M. Hillmyer, Polym. Chem. 5, 3507 (2014).
R. R. Schrock, Dalton Trans. 40, 7484 (2011).
A. Leitgeb, J. Wappel, and C. Slugovc, Polymer 51, 2927 (2010).
K. Nomura and M. M. Abdellatif, Polymer 51, 1861 (2010).
A. J. Teator and C. W. Bielawski, J. Polym. Sci., Part A: Polym. Chem. 55, 2949 (2017).
S. Sutthasupa, M. Shiotsuki, and F. Sanda, Polym. J. 42, 905 (2010).
J. P. Kennedy and H. S. Makowski, J. Macromol. Sci., Chem. 1, 345 (1967).
G. A. Olah, A. M. White, J. R. Demember, A. Commeyras, and C. Y. Lui, J. Am. Chem. Soc. 6, 4627 (1968).
N. Gaylord, A. Deshpande, B. Mandal, and M. Martan, J. Macromol. Sci., Chem. 11, 1053 (1977).
T. Sagane, A. Mizuno, and T. Takata, Makromol. Chem. 193, 2697 (1992).
M. V. Bermeshev, B. A. Bulgakov, A. M. Genaev, J. V. Kostina, G. N. Bondarenko, and E. S. Finkelshtein, Macromolecules 47, 5470 (2014).
W. Kaminsky, Adv. Polym. Sci. 258, 1 (2013).
E. S. Finkelshtein, K. L. Makovetskii, M. L. Gringolts, Y. V. Rogan, T. G. Golenko, V. G. Lakhtin, and M. P. Filatova, J. Mol. Catal. A: Chem. 257, 9 (2006).
C. Mehler and W. Risse, Macromolecules 25, 4226 (1992).
F. Blank, H. Scherer, and C. Janiak, J. Mol. Catal. A: Chem. 330, 1 (2010).
Z. Jiang and A. Sen, Organometallics 12, 1406 (1993).
Z. Jiang and A. Sen, J. Am. Chem. Soc. 112, 9655 (1990).
A. Sen and T. W. Lai, Organometallics 1, 415 (1982).
A. Sen and T.-W. Lai, J. Am. Chem. Soc. 103, 4627 (1981).
A. Sen and T. W. Lai, Inorg. Chem. 20, 4036 (1981).
N. Seehof, C. Mehler, S. Breunig, and W. Risse, J. Mol. Catal. 76, 219 (1992).
C. Mehler, S. Breunig, and W. Risse, Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 32, 337 (1991).
J. McDermott, C. Chang, L. F. Martín, L. F. Rhodes, G. M. Benedikt, and R. P. Lattimer, Macromolecules 41, 2984 (2008).
T. F. A. Haselwander, W. Heitz, S. Krugel, and J. Wendorff, Macromol. Chem. Phys. 197, 3435 (1996).
T. F. A. Haselwander, W. Heitz, S. A. Krugel, and J. Wendorff, Macromolecules 30, 5345 (1997).
A. S. Abu-surrah, K. Lappalainen, M. Kettunen, T. Repo, M. Leskela, H. A. Hodali, and B. Rieger, Macromol. Chem. Phys. 202, 599 (2001).
A. S. Abu-surrah, K. Lappalainen, T. Repo, M. Klinga, M. Leskela, and H. A. Hodali, Polyhedron 19, 1601 (2000).
C. Mehler and W. Risse, Makromol. Chem., Rapid Commun. 13, 455 (1992).
S. Breunig and W. Risse, Makromol. Chem. 193, 2915 (1992).
J. Melia, E. Connor, S. Rush, S. Breunig, C. Mehler, and W. Risse, Macromol. Symp. 89, 433 (1995).
R. Jira, Angew. Chem., Int. Ed. 48, 9034 (2009).
J. A. Keith and P. M. Henry, Angew. Chem., Int. Ed. 48, 9038 (2009).
W. J. Tao, J. F. Li, A. Q. Peng, X. L. Sun, X. H. Yang, and Y. Tang, Chem.-Eur. J. 19, 13956 (2013).
W. Clegg, G. R. Eastham, M. R. J. Elsegood, B. T. Heaton, J. A. Iggo, R. P. Tooze, R. Whyman, and S. Zacchini, Organometallics 21, 1832 (2002).
S. Mecking, Coord. Chem. Rev. 203, 325 (2000).
S. D. Ittel, L. K. Johnson, and M. S. Brookhart, Chem. Rev. 100, 1169 (2000).
A. L. Kocen, K. Klimovica, M. S. Brookhart, and O. Daugulis, Organometallics 36, 787 (2017).
J. M. Malinoski, P. S. White, and M. S. Brookhart, Organometallics 22, 621 (2003).
A. M. LaPointe and M. S. Brookhart, Organometallics 17, 1530 (1998).
S. Mecking, L. K. Johnson, L. Wang, and M. S. Brookhart, J. Am. Chem. Soc. 120 (4), 888 (1998).
M. D. Walter, P. S. White, and M. S. Brookhart, Chem. Commun. 2009, 6361 (2009).
K.-H. Yu, S.-L. Huang, Y.-H. Liu, Y. Wang, S.-T. Liu, Y.-C. Cheng, Y.-F. Lin, and J.-T. Chen, Molecules 22, 1095 (2017).
J. Deng, H. Gao, F. Zhu, and Q. Wu, Organometallics 32, 4507 (2013).
J. Kiesewetter, B. Arikan, and W. Kaminsky, Polymer 47, 3302 (2006).
Y. Chen, S. Mandal, and A. Sen, Organometallics 29, 3160 (2010).
M. Chen, W. Zou, Z. Cai, and C. Chen, Polym. Chem. 6, 2669 (2015).
M. Chen, B. Yang, and C. Chen, Angew. Chem., Int. Ed. 54, 15520 (2015).
M. Abubekerov, S. M. Shepard, and P. L. Diaconescu, Eur. J. Inorg. Chem. 2016, 2634 (2016).
B. Yang, W. Pang, and M. Chen, Eur. J. Inorg. Chem. 2017, 2510 (2017).
Zh. Uilki, B. Bogdanovich, R. Khardt, R. Khaimbakh, V. Kaim, M. Kroner, V. Oberkirkh, K. Tanaka, E. Shpgainryuke, D. Val’ter, and X. Tsimmerman, Usp. Khim. 37, 1056 (1968).
H. Kurosawa, J. Organomet. Chem. 334, 243 (1987).
P. W. Jolly, Angew. Chem., Int. Ed. Engl. 24, 283 (1985).
V. R. Flid, E. M. Evstigneeva, O. Yu. Tkachenko, and R. S. Shamsiev, Ross. Khim. Zh. 50 (4), 93 (2006).
Promerus. www.promerus.com/technology. Cited 2019.
W. Kaminsky and M. Arndt-Rosenau, in Stereoselective Polymerization with Single-Site Catalysts, Ed by. L. S. Baugh and J. A. M. Canich (CRC Press, Boca Raton, FL, 2007), p. 413.
M. D. Walter, R. A. Moorhouse, P. S. White, and M. S. Brookhart, J. Polym. Sci., Part A: Polym. Chem. 47, 2560 (2009).
M. D. Walter, R. A. Moorhouse, S. A. Urbin, P. S. White, M. S. Brookhart, and N. Carolina, J. Am. Chem. Soc. 131, 9055 (2009).
J. Potier, B. Commarieu, A. Soldera, and J. P. Claverie, ACS Catal. 8, 6047 (2018).
T. X. Zhang, M. R. Xia, Z. Li, and B. Q. Mao, Comput. Theor. Chem. 997, 110 (2012).
B. L. Goodall, G. M. Benedikt, L. H. McIntosh, III, and D. A. Barnes, US Patent No. 5468819 (1995).
B. S. Heinz, F. P. Alt, and W. Heitz, Macromol. Rapid Commun. 19, 251 (1998).
A. D. Hennis, J. D. Polley, G. S. Long, A. Sen, D. Yandulov, J. Lipian, G. M. Benedikt, L. F. Rhodes, and J. Huffman, Organometallics 20, 2802 (2001).
Y. Huang, J. He, Z. Liu, G. Cai, S. Zhang, and X. Li, Polym. Chem. 8, 1217 (2017).
S. Kaita, K. Matsushita, M. Tobita, Y. Maruyama, and Y. Wakatsuki, Macromol. Rapid Commun. 27, 1752 (2006).
E. A. Bielinski, W. Dai, L. M. Guard, N. Hazari, and M. K. Takase, Organometallics 32, 4025 (2013).
W. Zou, W. Pang, and C. Chen, Inorg. Chem. Front. 4, 795 (2017).
J. P. Mathew, A. Reinmuth, J. Melia, N. Swords, and W. Risse, Macromolecules 29, 2755 (1996).
N. Seehof, C. Mehler, S. Breunig, and W. Risse, J. Mol. Catal. 76, 53 (1992).
K. Müller, Y. Jung, D. Y. Yoon, S. Agarwal, A. Greiner, Macromol. Chem. Phys. 211, 1595 (2010).
S. V. Mulpuri, J. Shin, B. G. Shin, A. Greiner, and D. Y. Yoon, Polymer 52, 4377 (2011).
B. Liu, X. Wang, Y. Wang, W. Yan, H. Li, and I. Kim, React. Funct. Polym. 69, 606 (2009).
J. H. Park, T. W. Koh, Y. Do, M. H. Lee, and S. Yoo, J. Polym. Sci., Part A: Polym. Chem. 50, 2356 (2012).
M. Eo, S. Lee, M. H. Park, M. H. Lee, S. Yoo, and Y. Do, Macromol. Rapid Commun. 33, 1119 (2012).
J. H. Park, C. Yun, T.-W. Koh, Y. Do, S. Yoo, and M. H. Lee, J. Mater. Chem. 21, 5422 (2011).
E. S. Finkelshtein, M. V. Bermeshev, M. L. Gringolts, L. E. Starannikova, and Y. P. Yampolskii, Russ. Chem. Rev. 80, 341 (2011).
M. Gringolts, M. Bermeshev, Y. Yampolskii, L. Starannikova, V. Shantarovich, and E. Finkelshtein, Macromolecules 43, 7165 (2010).
B. Commarieu and J. P. Claverie, Chem. Sci. 6, 2172 (2015).
K. H. Kim, Y.-K. Han, S. U. Lee, S.-H. Chun, and J. H. Ok, J. Mol. Model. 9, 304 (2003).
I. Takamiya, M. Yamashita, and K. Nozaki, Organometallics 27, 5347 (2008).
H. Tetsuka, M. Hagiwara, and S. Kaita, Polym. J. 43, 97 (2010).
M. H. Park, C. Yun, J. O. Huh, Y. Do, S. Yoo, and M. H. Lee, Synth. Met. 160, 2000 (2010).
D. S. Suslov, M. V. Bykov, A. V. Kuzmin, P. A. Abramov, O. V. Kravchenko, M. V. Pakhomova, A. V. Rokhin, I. A. Ushakov, and V. S. Tkach, Catal. Commun. 106, 30 (2018).
M. Yamashita, I. Takamiya, K. Jin, and K. Nozaki, Organometallics 25, 4588 (2006).
V. S. Tkach, F. K. Shmidt, and N. A. Gulaya, Izobret., Polezn. Modeli 16, 378 (2001).
V. S. Tkach, S. N. Zelinskii, G. V. Ratovskii, A. G. Proidakov, and F. K. Schmidt, Russ. J. Coord. Chem. 30, 703 (2004).
G. Myagmarsuren, Extended Abstract of Doctoral Dissertation in Chemistry (Irkutskii Gos. Univ., Irkutsk, 2008).
M. L. Chernyshev, V. S. Tkach, T. V. Dmitrieva, G. V. Ratovskii, S. V. Zinchenko, and F. K. Shmidt, Kinet. Katal. 38, 575 (1997).
V. S. Tkach, G. V. Ratovskii, T. V. Dmitrieva, N. D. Malakhova, and F. K. Shmidt, Koord. Khim. 10, 1687 (1984).
V. S. Tkach, G. V. Ratovskii, G. Myagmarsuren, M. Mes’ef, O. V. Tyukalova, S. N. Zelinskii, and F. K. Shmidt, Koord. Khim. 26, 219 (2000).
A. V. Bobkova, S. N. Zelinskii, G. V. Ratovskii, V. S. Tkach, and F. K. Shmidt, Kinet. Catal. 42, 189 (2001).
V. S. Tkach, F. K. Shmidt, T. V. Dmitrieva, G. V. Ratovskii, N. D. Malakhova, N. A. Murasheva, G. Myagmarsuren, Koord. Khim. 14, 1424 (1988).
V. S. Tkach, F. K. Shmidt, U. M. Dzhemilev, G. V. Ratovskii, M. L. Chernyshev, and O. I. Burlakova, Koord. Khim. 15, 1395 (1989).
M. L. Chernyshev, V. S. Tkach, T. V. T. Dmitrieva, G. V. Ratovskii, S. V. S. Zinchenko, and F. K. Shmidt, React. Kinet. Catal. Lett. 48, 291 (1992).
V. S. Tkach, G. Myagmarsuren, M. Mesyef, and F. K. Shmidt, React. Kinet. Catal. Lett. 66, 281 (1999).
G. Myagmarsuren, V. S. Tkach, and F. K. Shmidt, React. Kinet. Catal. Lett. 83, 337 (2004).
G. Myagmarsuren, K. Lee, O. Jeong, and S. Ihm, Catal. Commun. 4, 615 (2003).
G. Myagmarsuren, K. S. Lee, O. Y. Jeong, and S. K. Ihm, Polymer 45, 3227 (2004).
G. Myagmarsuren, O.-Y. Jeong, and S. Ihm, Appl. Catal., A 296, 21 (2005).
G. Myagmarsuren, K. S. Lee, O. Y. Jeong, and S. K. Ihm, Polymer 46, 3685 (2005).
V. S. Tkach, G. Myagmarsuren, D. S. Suslov, and F. K. Shmidt, Russ. J. Gen. Chem. 77, 489 (2007).
G. Myagmarsuren, V. S. Tkach, D. S. Suslov, and F. K. Shmidt, Russ. J. Appl. Chem. 80, 252 (2007).
G. Myagmarsuren, J. Il. Park, and S. K. Ihm, Polymer 47, 8474 (2006).
C. Chang, J. Lipian, D. A. Barnes, L. Seger, C. Burns, B. Bennett, L. Bonney, L. F. Rhodes, G. M. Benedikt, R. Lattimer, S. S. Huang, and V. W. Day, Macromol. Chem. Phys. 206, 1988 (2005).
H. Morishita, A. Sudo, and T. Endo, J. Polym. Sci., Part A: Polym. Chem. 47, 3982 (2009).
N. Thirupathi, D. Amoroso, A. Bell, and J. D. Protasiewicz, J. Polym. Sci., Part A: Polym. Chem. 47, 103 (2009).
C. Chang, J. Lipian, C. Burns, L. F. Rhodes, and R. P. Lattimer, J. Photopolym. Sci. Technol. 23, 715 (2010).
A. Sudo, H. Morishita, and T. Endo, J. Polym. Sci., Part A: Polym. Chem. 48, 3896 (2010).
C. Chang, D. Barnes, L. D. Seger, L. F. Rhodes, R. P. Lattimer, and G. M. Benedikt, J. Photopolym. Sci. Technol. 25, 161 (2012).
P. Kandanarachchi, C. Chang, S. Smith, P. Bradley, L. F. Rhodes, R. P. Lattimer, and G. M. Benedikt, J. Photopolym. Sci. Technol. 26, 431 (2013).
C. Chang, A. Bell, R. A. Shick, L. D. Seger, L. F. Rhodes, and G. M. Benedikt, J. Photopolym. Sci. Technol. 27, 497 (2014).
S. Okeya, H. Sazaki, M. Ogita, T. Takemoto, Y. Onuki, Y. Nakamura, B. K. Mohapatra, and S. Kawaguchi, Bull. Chem. Soc. Jpn. 54, 1978 (1981).
S. Baba, T. Ogura, and S. Kawaguchi, Bull. Chem. Soc. Jpn. 47, 665 (1974).
V. S. Tkach, D. S. Suslov, G. Myagmarsuren, G. V. Ratovskii, A. V. Rohin, F. Tuczek, and F. K. Shmidt, J. Organomet. Chem. 693, 2069 (2008).
D. S. Suslov, M. V. Bykov, M. V. Belova, P. A. Abramov, and V. S. Tkach, J. Organomet. Chem. 752, 37 (2014).
V. S. Tkach, D. S. Suslov, N. V. Kurat’eva, M. V. Bykov, M. V. Belova, M. V. Bykov, and M. V. Belova, Russ. J. Coord. Chem. 37, 752 (2011).
D. S. Suslov, M. V. Pakhomova, M. V. Bykov, and V. S. Tkach, Russ. J. Gen. Chem. 84, 2291 (2014).
D. S. Suslov, M. V. Pahomova, P. A. Abramov, M. V. Bykov, and V. S. Tkach, Catal. Commun. 67, 11 (2015).
D. S. Suslov, M. V. Bykov, P. A. Abramov, M. V. Pakho-mova, I. A. Ushakov, V. K. Voronov, and V. S. Tkach, Inorg. Chem. Commun. 66, 1 (2016).
M. V. Bykov, Extended Abstract of Candidate’s Dissertation in Chemistry (Irkutskii Gos. Univ., Irkutsk, 2013).
N. V. Kuratieva, V. S. Tkach, D. S. Suslov, M. V. Bykov, and S. A. Gromilov, J. Struct. Chem. 52, 813 (2011).
D. S. Suslov, M. V. Bykov, G. V. Ratovskii, P. A. Abramov, M. V. Pahomova, I. A. Ushakov, V. K. Voronov, and V. S. Tkach, J. Mol. Struct. 1133, 411 (2017).
D. S. Suslov, M. V. Bykov, P. A. Abramov, M. V. Pahomova, I. A. Ushakov, V. K. Voronov, and V. S. Tkach, RSC Adv. 5, 104467 (2015).
V. S. Tkach, D. S. Suslov, N. V. Kurat’eva, M. V. Bykov, and M. V. Belova, Russ. J. Coord. Chem. 37, 752 (2011).
K. Jonas and G. Wilke, Angew. Chem., Int. Ed. Eng. 8, 519 (1969).
C. A. Tolman, J. Am. Chem. Soc. 92, 6777 (1970).
C. A. Tolman, J. Am. Chem. Soc. 92, 4217 (1970).
C. A. Tolman, J. Am. Chem. Soc. 94, 2994 (1972).
C. A. Tolman, J. Am. Chem. Soc. 92, 6785 (1970).
F. K. Shmidt, L. V. Mironova, A. G. Proidakov, and A. V. Kalabina, Koord. Khim. 4, 1608 (1978).
F. K. Shmidt, L. V. Mironova, A. G. Proidakov, G. A. Kalabin, G. V. Ratovskii, and T. V. Dmitrieva, Kinet. Katal. 19, 150 (1978).
F. K. Shmidt, Catalysis by Complexes of First Row Transition Metals of Hydrogenation and Dimerization Reactions (Izd-vo Irkutskogo Gos. Univ., Irkutsk, 1986) [in Russian].
A. H. Nesmeyanov, F. K. Shmidt, L. V. Mironova, L. S. Isaeva, L. N. Lorens, and A. G. Proidakov, Dokl. Akad. Nauk SSSR, Ser. Khim. 233, 379 (1977).
G. Myagmarsuren, O. Jeong, and S. K. Ihm, Appl. Catal., A 255, 203 (2003).
G. Myagmarsuren, O. Y. Jeong, and S. Ihm, Appl. Catal., A 275, 271 (2004).
F. K. Schmidt, L. B. Belykh, M. Gomboogiin, and Y. Y. Titova, Kinet. Catal 51, 235 (2010).
F. K. Shmidt, Y. Y. Titova, L. B. Belykh, M. Gomboogiin, J. J. Titova, L. B. Belykh, and M. Gomboogiin, Pet. Chem. 50, 205 (2010).
V. S. Tkach, D. S. Suslov, G. Myagmarsuren, O. V. Gubaidulina, and M. V. Bykov, Russ. J. Gen. Chem. 79, 323 (2009).
V. S. Tkach, D. S. Suslov, G. Myagmarsuren, O. V. Gubaydulina, M. V. Bykov, and V. A. Umanets, Catal. Commun. 10, 1813 (2009).
V. S. Tkach, D. S. Suslov, O. V. Gubaidulina, M. V. Bykov, and O. I. Mis’ko, RF Patent No. 2414965 (2011).
V. S. Tkach, D. S. Suslov, O. V. Gubaidulina, M. V. Bykov, M. V. Belova, and O. I. Mis’ko, RF Patent No. 2487896 (2013).
V. S. Tkach, D. S. Suslov, O. V. Gubaidulina, M. V. Bykov, M. V. Belova, and O. I. Mis’ko, RF Patent No. 2487895 (2013).
Y. Jang, H.-K. Sung, S. Lee, and C. Bae, Polymer 46, 11301 (2005).
P. B. Kraikivskii, V. V. Saraev, V. V. Bocharova, D. A. Matveev, S. K. Petrovskii, and M. D. Gotsko, Catal. Commun. 12, 634 (2011).
V. V. Saraev, P. B. Kraikivskii, V. V. Bocharova, and D. A. Matveev, Kinet. Catal. 53, 486 (2012).
C. Janiak, P. Lassahn, and V. Lozan, Macromol. Symp. 236, 88 (2006).
R. Zhuang, H. Liu, J. Guo, B. Dong, W. Zhao, Y. Hu, and X. Zhang, Eur. Polym. J. 93, 358 (2017).
Y. Kong, H. Ren, S. Xu, H. Song, B. Liu, and B. Wang, Organometallics 28, 5934 (2009).
Y. Kong, L. Wen, H. Song, S. Xu, M. Yang, B. Liu, and B. Wang, Organometallics 30, 153 (2011).
L. Dang, J. Guo, H. Song, B. Liu, and B. Wang, Dalton Trans. 43, 17177 (2014).
M. Li, H. Song, and B. Wang, Organometallics 34, 1969 (2015).
D. Yang, Y. Tang, H. Song, and B. Wang, Organometallics 35, 1392 (2016).
D. Yang, Y. Tang, H. Song, and B. Wang, Organometallics 35, 1392 (2016).
L. Dang, J. Guo, H. Song, B. Liu, and B. Wang, Dalton Trans 43, 17177 (2014).
W. Zhang, Y. Wang, J. Yu, C. Redshaw, X. Hao, and W.-H. Sun, Dalton Trans. 40, 12856 (2011).
S. Jie, P. Ai, Q. Zhou, and B. G. Li, J. Organomet. Chem. 696, 1465 (2011).
T. Zheng, H. Liao, J. Gao, L. Zhong, H. Gao, and Q. Wu, Polym. Chem. 9, 3088 (2018).
J. Tian, X. He, J. Liu, X. Deng, and D. Chen, RSC Adv. 6, 22908 (2016).
Y. Zeng, Q. Mahmood, Q. Zhang, T. Liang, and W.‑H. Sun, J. Polym. Sci., Part A: Polym. Chem. 56, 922 (2018).
Y. Zeng, Q. Mahmood, Q. Zhang, T. Liang, and W.‑H. Sun, Eur. Polym. J. 103, 342 (2018).
A. Sachse, S. Demeshko, S. Dechert, V. Daebel, A. Lange, and F. Meyer, Dalton Trans. 39, 3903 (2010).
J. He, Z. Liu, G. Du, Y. Fu, S. Zhang, and X. Li, Organometallics 33 (21), 6103 (2014).
A. Li, J. Chen, L. Zhang, Z. Li, M. Zhu, W. Zhang, X. Lin, and Z. Zhang, J. Appl. Polym. Sci. 113, 1642 (2009).
M. Li, X. Shu, Z. Cai, and M. S. Eisen, Organometallics 37, 1172 (2018).
Y. L. Qiao and G. X. Jin, Organometallics 32, 1932 (2013).
P.-G. Lassahn, V. Lozan, and C. Janiak, Dalton Trans. 2003, 927 (2003).
O. Jana and G. Mani, Inorg. Chem. 57, 7735 (2018).
Q. Feng, D. Chen, D. Feng, L. Jiao, Z. Peng, and L. Pei, Appl. Organomet. Chem. 28, 32 (2014).
Y. Yu, J. Chen, S. Meng, C. Li, M. Lan, and Z. Zhang, J. Mol. Catal. A:Chem. 380, 104 (2013).
Z. Zhou, X. Hao, C. Redshaw, L. Chen, and W.-H. Sun, Catal. Sci. Technol. 2, 1340 (2012).
Y. Guo, P. Ai, L. Han, L. Chen, B.-G. Li, and S. Jie, J. Organomet. Chem. 716, 222 (2012).
Y.-M. Xu, K. Li, Y. Wang, W. Deng, and Z.-J. Yao, Polymers 9, 105 (2017).
D.-P. Song, Y.-G. Li, R. Lu, N.-H. Hu, and Y. Li, Appl. Organomet. Chem. 22, 333 (2008).
J. Wang, L. Wan, D. Zhang, Q. Wang, and Z. Chen, Eur. J. Inorg. Chem. 2013, 2093 (2013).
Z. Hao, N. Yang, W. Gao, L. Xin, X. Luo, and Y. Mu, J. Organomet. Chem. 749, 350 (2014).
X. C. Shi and G. X. Jin, Organometallics 31, 4748 (2012).
H. Gao, L. Pei, Y. Li, J. Zhang, and Q. Wu, J. Mol. Catal. A: Chem. 280, 81 (2008).
J. K. Zhang, P. C. Wang, X. W. Wang, L. Wang, J. C. Chen, Z. W. Zheng, and Y. P. Niu, J. Organomet. Chem. 696, 3697 (2011).
H. Gao, Y. Liu, G. Li, Z. Xiao, G. Liang, Q. Wu, Polym. Chem. 5, 6012 (2014).
V. Appukuttan, J. H. Kim, C. S. Ha, and I. Kim, Korean J. Chem. Eng. 25, 423 (2008).
Y.-P. Niu, X.-W. Wang, Z.-W. Zheng, X.-F. Ma, J.‑Q. Cai, J.-K. Zhang, and J.-L. Cheng, Appl. Organomet. Chem. 28, 688 (2014).
A. Antonov, N. V. Semikolenova, V. Zakharov, W. Zhang, Y. Wang, W.-H. Sun, E. P. Talsi, and K. P. Bryliakov, Organometallics 31, 1143 (2012).
Y. Huang, J. Chen, L. Chi, C. Wei, Z. Zhang, Z. Li, A. Li, and L. Zhang, J. Appl. Polym. Sci. 112, 1486 (2009).
Y.-Y. Wang, S.-A. Lin, F.-M. Zhu, H.-Y. Gao, and Q. Wu, J. Appl. Polym. Sci. 110, 3590 (2008).
Y. Y. Wang, B. X. Li, F. M. Zhu, H. Y. Gao, and Q. Wu, Polym. Bull. 70, 681 (2013).
Y. Y. Wang, S. Lin, F. M. Zhu, H. Y. Gao, and Q. Wu, Eur. Polym. J. 44, 2308 (2008).
A. O. Eseola, M. Zhang, J. F. Xiang, W. Zuo, Y. Li, J. A. O. Woods, and W. H. Sun, Inorg. Chim. Acta 363, 1970 (2010).
F. Han, Y. Zhang, X. Sun, B. Li, Y. Guo, and Y. Tang, Organometallics 27, 1924 (2008).
F. S. Liu, H. Y. Gao, K. M. Song, Y. Zhao, J. M. Long, L. Zhang, F. M. Zhu, and Q. Wu, Polyhedron 28, 673 (2009).
J. Berding, M. Lutz, A. L. Spek, and E. Bouwman, Appl. Organomet. Chem. 25, 76 (2011).
D. Zhang, S. Zhou, Z. Li, Q. Wang, and L. Weng, Dalton Trans. 42, 12020 (2013).
Y. Kong, M. Cheng, H. Ren, S. Xu, H. Song, M. Yang, B. Liu, and B. Wang, Organometallics 30, 1677 (2011).
H. Song, D. Fan, Y. Liu, G. Hou, and G. Zi, J. Organomet. Chem. 729, 40 (2013).
K. Vijayakrishna, S. Padmanabhan, T. Kannan, and D. Dakshinamoorthy, Polym. Bull. 68, 635 (2012).
E. S. Finkelshtein, K. L. Makovetskii, M. L. Gringolts, Y. V. Rogan, T. G. Golenko, L. E. Starannikova, Y. P. Yampolskii, V. P. Shantarovich, and T. Suzuki, Macromolecules 39, 7022 (2006).
K. L. Makovetskii, L. I. Gorbacheva, T. G. Golenko, and I. Ya. Ostrovskaya, Vysokomol. Soedin., Ser. A 38, 435 (1996).
A. A. Antonov, D. G. Samsonenko, E. P. Talsi, and K. P. Bryliakov, Organometallics 32, 2187 (2013).
F. Blank, J. K. Vieth, J. Ruiz, V. Rodríguez, and C. Janiak, J. Organomet. Chem. 696, 473 (2011).
F. Blank, H. Scherer, J. Ruiz, V. Rodríguez, C. Janiak, Dalton Trans. 39, 3609 (2010).
Z.-J. Yao, P. Li, K. Li, and W. Deng, Appl. Organomet. Chem. 32, (2018). https://doi.org/10.1002/aoc.4239
J. Meng, X. Li, X. Ni, and Z. Shen, Polym. Int. 66, 1617 (2017).
Z. Chu, L. Q. Ding, Y. Long, L. L. Chen, X. Q. Lü, J. R. Song, D. Di. Fan, F. Bao, and R. Ma, J. Inorg. Organomet. Polym. Mater. 20, 235 (2010).
D. A. Barnes, G. M. Benedikt, B. L. Goodall, S. S. Huang, H. A. Kalamarides, S. Lenhard, L. H. McIntosh, K. T. Selvy, R. A. Shick, and L. F. Rhodes, Macromolecules 36, 2623 (2003).
D.-P. Song, H.-L. Mu, X.-C. Shi, Y.-G. Li, and Y.-S. Li, J. Polym. Sci., Part A: Polym. Chem. 50, 562 (2012).
P. Huo, W. Liu, X. He, H. Wang, and Y. Chen, Organometallics 32, 2291 (2013).
T. Yamamoto, C. Shikada, S. Kaita, T. Olivier, Y. Maruyama, and Y. Wakatsuki, J. Mol. Catal. A: Chem. 300, 1 (2009).
B. Yuan, X. He, Y. Chen, and K. Wang, Macromol. Chem. Phys. 212, 2378 (2011).
X. He, B. Yuan, Y. Chen, and D. Chen, High Perform. Polym. 25, 287 (2012).
R. Huang, X. He, Y. Chen, H. Nie, and W. Zhou, Polym. Adv. Technol. 23, 483 (2012).
J. Tian, H. Zhu, J. Liu, D. Chen, and X. He, Appl. Organomet. Chem. 28, 702 (2014).
X. He, Y. Liu, L. Chen, Y. Chen, and D. Chen, J. Polym. Sci., Part A: Polym. Chem. 50, 4695 (2012).
Y. Liu, M. Ouyang, X. He, Y. Chen, and K. Wang, J. Appl. Polym. Sci. 128, 216 (2013).
L. Chen, Z. Zhong, C. Chen, X. He, and Y. Chen, J. Organomet. Chem. 752, 100 (2014).
Y. Xing, Y. Chen, X. He, and H. Nie, J. Appl. Polym. Sci. 124, 1323 (2012).
M. Hu, X. He, Y. Chen, and D. Chen, J. Polym. Res. 19, article 9977 (2012).
P. Huo, J. Li, W. Liu, G. Mei, and X. He, RSC Adv. 7, 51858 (2017).
Funding
This study was supported by the Russian Foundation for Basic Research and the Government of the Irkutsk oblast (project code 17-43-380010). It was carried in the framework of the main part of the State Task in the Field of Scientific Activities of the Ministry of Education and Science of the Russian Federation (no. 4.9489.2017/8.9).
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Suslov, D.S., Bykov, M.V. & Kravchenko, O.V. Norbornene Addition Polymerization with Catalysts Based on Transition Metal Compounds: 2008–2018. Polym. Sci. Ser. C 61, 145–173 (2019). https://doi.org/10.1134/S181123821901017X
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DOI: https://doi.org/10.1134/S181123821901017X