3,4-polymerization of isoprene by using NSN- and NPN-ligated rare earth metal precursors: Switching of stereo selectivity and mechanism

Macromolecules

Volumn 47, Issue 15, 2014, Pages 4971-4978

  Liu, Bo ^a,b   Li, Lei ^a,d   Sun, Guangping ^b   Liu, Jingyao ^c   Wang, Meiyan ^c   Li, Shihui ^a   Cui, Dongmei ^a  

^a CHANGCHUN INSTITUTE OF APPLIED CHEMISTRY   (China)

^b Jilin University   (China)

^c JILIN UNIVERSITY   (China)

^d UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ISOPRENE; LIGANDS; LITHIUM; METAL COMPLEXES; POLYMERIZATION; SCANDIUM; X RAY DIFFRACTION ANALYSIS;

ALKYL GROUPS; DIALKYL COMPLEXES; EQUIMOLAR AMOUNT; ION PAIRS; ISOSPECIFIC; LITHIUM SALTS; RARE-EARTH METALS;

PRASEODYMIUM;

EID: 84905908292     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/ma501085c     Document Type: Article

References (92)

1. Alt, H.; Samuel, E. Chem. Soc. Rev. 1998, 27, 323-329
2. Alt, H.; Köppl, A. Chem. Rev. 2000, 100, 1205-1221
3. Resconi, L.; Cavallo, L.; Fait, A.; Piemontesi, F. Chem. Rev. 2000, 100, 1253-1345
4. Gibson, V.; Spitzmesser, S. Chem. Rev. 2003, 103, 283-315
5. Makio, H.; Terao, H.; Iwashita, A.; Fujita, T. Chem. Rev. 2011, 111, 2363-2449
6. Shen, Z.; Ouyang, J. In Handbook of the Physics and Chemistry of Rare Earth; Gschneidner, K.; Fleming, L., Eds.; Elsevier: Amsterdam, 1987; p 61.
7. Hou, Z.; Wakatsuki, Y. Coord. Chem. Rev. 2002, 231, 1-22
8. Arndt, S.; Okuda, J. Adv. Synth. Catal. 2005, 347, 339-354
9. Fischbach, A.; Anwander, R. Adv. Polym. Sci. 2006, 204, 155-281
10. Zhang, Z.; Cui, D.; Wang, B.; Liu, B.; Yang, Y. Struct. Bonding (Berlin) 2010, 137, 49-108
11. Nishiura, M.; Hou, Z. Nat. Chem. 2010, 2, 257-268
12. Zimmermann, M.; Anwander, R. Chem. Rev. 2010, 110, 6194-6259
13. Valente, A.; Mortreux, A.; Visseaux, M.; Zinck, P. Chem. Rev. 2013, 113, 3836-3857
14. Scott, K. Rubber Plast. Age 1961, 42, 175
15. Evans, W.; Giarikos, D.; Ziller, J. Organometallics 2001, 20, 5751-5758
16. Meermann, C.; Tornroos, K.; Nerdal, W.; Anwander, R. Angew. Chem., Int. Ed. 2007, 46, 6508-6513
17. Zhang, L.; Suzuki, T.; Luo, Y.; Nishiura, M.; Hou, Z. Angew. Chem., Int. Ed. 2007, 46, 1909-1913
18. Gao, W.; Cui, D. J. Am. Chem. Soc. 2008, 130, 4984-4991
19. Wang, L.; Cui, D.; Hou, Z.; Li, W.; Li, Y. Organometallics 2011, 30, 760-767
20. Wang, L.; Liu, D.; Cui, D. Organometallics 2013, 31, 6014-6021
21. Baudry-Barbier, D.; Andre, N.; Dormond, A.; Pardes, C.; Richard, P.; Visseaux, M.; Zhu, C. Eur. J. Inorg. Chem. 1998, 1721-1727
22. Bonnet, F.; Visseaux, M.; Pereira, A.; Barbier-Baudry, D. Macromolecules 2005, 38, 3162-3169
23. Milione, S.; Cuomo, C.; Capacchione, C.; Zannoni, C.; Grassi, A.; Proto, A. Macromolecules 2007, 40, 5638-5643
24. Zimmermann, M.; Tornroos, K. W.; Anwander, R. Angew. Chem., Int. Ed. 2008, 47, 775-778
25. Yang, Y.; Lv, K.; Wang, L.; Wang, Y.; Cui, D. Chem. Commun. 2010, 46, 6150-6152
26. Liu, D.; Cui, D. Dalton Trans. 2011, 40, 7755-7761
27. Rong, W.; Liu, D.; Zuo, H.; Pan, Y.; Jian, Z.; Li, S.; Cui, D. Organometallics 2013, 32, 1166-1175
28. Liu, H.; He, J.; Liu, Z.; Lin, Z.; Du, G.; Zhang, S.; Li, X. Macromolecules 2013, 46, 3257-3265
29. Ueno, H.; Oizumi, K.; Ishikawa, H.; Nakajima, K.; Tsujimoto, N.; Kimura, O.; Aikawa, H. U.S. Patent 4 153 767, 1979.
30. Ashitaka, H.; Jinda, K.; Ueno, H. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1989-1995
31. Ricci, G.; Forni, A.; Boglia, A.; Motta, T.; Zannoni, G.; Canetti, M.; Bertini, F. Macromolecules 2005, 38, 1064-1070
32. Tang, Y.; Dai, Q.; Zhang, X. Chin. J. Appl. Chem. 2013, 30, 11-15
33. Zhang, L.; Luo, Y.; Hou, Z. J. Am. Chem. Soc. 2005, 127, 14562-14563
34. Wang, B.; Cui, D.; Lv, K. Macromolecules 2008, 41, 1983-1988
35. Li, S.; Miao, W.; Tang, T.; Dong, W.; Zhang, X.; Cui, D. Organometallics 2008, 27, 718-725
36. Zhang, L.; Nishiura, M.; Yuki, M.; Luo, Y.; Hou, Z. Angew. Chem., Int. Ed. 2008, 47, 2642-2645
37. Li, S.; Cui, D.; Li, D.; Hou, Z. Organometallics 2009, 28, 4814-4822
38. Doring, C.; Kretschmer, W. P.; Bauer, T.; Kempe, R. Eur. J. Inorg. Chem. 2009, 4255-4264
39. Du, G.; Wei, Y.; Ai, L.; Chen, Y.; Xu, Q.; Liu, X.; Zhang, W.; Hou, Z.; Li, X. Organometallics 2011, 30, 160-170
40. Yao, C.; Liu, D.; Li, P.; Wu, C.; Li, S.; Liu, B.; Cui, D. Organometallics 2014, 33, 684-691
41. Bazzini, C.; Giarrusso, A.; Porri, L. Macromol. Rapid Commun. 2002, 23, 922-927
42. Bazzini, C.; Giarrusso, A.; Porri, L.; Pirozzi, B.; Napolitano, R. Polymer 2004, 45, 2871-2875
43. Ricci, G.; Battistella, M.; Bertini, F.; Porri, L. Polym. Bull. 2002, 48, 25-31
44. Ricci, G.; Battistella, M.; Porri, L. Macromolecules 2001, 34, 5766-5769
45. Wild, F.; Zsolnai, L.; Huttner, G.; Brintzinger, H. J. Organomet. Chem. 1982, 232, 233-247
46. Ewen, J. J. Am. Chem. Soc. 1984, 106, 6355-6364
47. Giannetti, E.; Nicoletti, G.; Mazzocchi, R. J. Polym. Sci., Polym. Chem. 1985, 23, 2117
48. De Rosa, C.; Auriemma, F.; Vinti, V.; Galimberti, M. Macromolecules 1998, 31, 6206-6210
49. Golub, M. Macromolecules 1969, 2, 550-552
50. Ogawa, M.; Araki, T.; Yamamoto, S. U.S. Patent 4,274,462, 1981.
51. Sheppard, C. U.S. Patent 4,338,225, 1982.
52. Ashitaka, H.; Kusuki, Y.; Asano, Y.; Yamamoto, S.; Ueno, H.; Nagasaka, A. J. Polym. Sci.: Polym. Chem. Ed. 1983, 21, 1111-1124
53. Selinka, C.; Deuerlein, S.; Hauser, T.; Stalke, D. Inorg. Chim. Acta 2004, 357, 1873-1880
54. Ding, Y.; Weber, P. J. Org. Chem. 1987, 52, 4625-4626
55. Spencer, L. P.; Altwer, R.; Wei, P. R.; Gelmini, L.; Gauld, J.; Stephan, D. W. Organometallics 2003, 22, 3841-5854
56. Stasch, A. Chem. - Eur. J. 2012, 18, 15105-15112
57. Jian, Z.; Cui, D.; Hou, Z. Chem. - Eur. J. 2012, 18, 2674-2684
58. Pan, Y.; Rong, W.; Jian, Z.; Cui, D. Macromolecules 2012, 48, 1248-1253
59. Li, X.; Nishiura, M.; Hu, L.; Mori, K.; Hou, Z. J. Am. Chem. Soc. 2009, 131, 13870-3882
60. Kang, X.; Song, Y.; Luo, Y.; Li, G.; Hou, Z.; Qu, J. Macromolecules 2012, 45, 640-651
61. Luo, Y.; Luo, Y.; Qu, J.; Hou, Z. Organometallics 2011, 30, 2908-2919
62. Li, X.; Wang, X.; Tong, X.; Zhang, H.; Chen, Y.; Liu, Y.; Liu, H.; Wang, X.; Nishiura, M.; He, H.; Lin, Z.; Zhang, S.; Hou, Z. Organometallics 2013, 32, 1445-1458
63. Li, X.; Nishiura, M.; Mori, K.; Mashiko, T.; Hou, Z. Chem. Commun. 2007, 4137-4139
64. Bambirra, S.; Leusen, D.; Meetsman, A.; Hessen, B.; Teuben, J. Chem. Commun. 2003, 522-523
65. Bambirra, S.; Bouwkamp, M.; Meetsman, A.; Hessen, B. J. Am. Chem. Soc. 2004, 126, 9182-9183
66. Zhao, W.; Cui, D.; Liu, X.; Chen, X. Macromolecules 2010, 43, 6678-6684
67. Li, D.; Li, S.; Wu, C.; Yao, C.; Cui, D. Acta Polym. Sin. 2013, 5, 649-653
68. Pan, Y.; Xie, H.; Cui, D. Chin. J. Appl. Chem. 2012, 29, 1389-1393
69. Coates, G. Chem. Rev. 2000, 100, 1223-1252
70. Resconi, L.; Cavallo, L.; Fait, A.; Piemontesi, F. Chem. Rev. 2000, 100, 1253-1345
71. Veghini, D.; Henling, L. M.; Burkhardt, T. J.; Bercaw, J. E. J. Am. Chem. Soc. 1999, 121, 564-573
72. Ewen, J. A.; Jones, R. L.; Razavi, A.; Ferrara, J. D. J. Am. Chem. Soc. 1988, 110, 6255-6256
73. GÓmez, F.; Waymouth, R. Macromolecules 2002, 35, 3358-3368
74. Ricci, G. Macromol. Symp. 1995, 89, 383-392
75. Ricci, G.; Battistella, M. Macromolecules 2001, 34, 5766-5769
76. Giarrussoa, A.; Porri, L.; Ricci, G. Macromol. Symp. 2002, 178, 55-68
77. Riccia, G.; Sommazzi, A.; Masi, F.; Ricci, M.; Boglia, A.; Leone, G. Coord. Chem. Rev. 2010, 254, 661-676
78. Coevoet, D.; Cramail, H.; Deffieux, A. Macromol. Chem. Phys. 1999, 200, 1208-1214
79. Vokis, V.; Smolensky, E.; Lisovskii, A.; Eisen, M. J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 4505-4516
80. Chen, M.; Marks, T. J. J. Am. Chem. Soc. 2001, 123, 11803-11804
81. Herzog, T. A.; Zubris, D. L.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 11988-11989
82. Murata, S.; Abe, S.; Tomioka, H. J. Org. Chem. 1997, 62, 3055-3061
83. Dilworth, J. R.; Herderson, R. A. J. Chem. Soc., Dalton. Trans. 1987, 529-540
84. Kaul, F.; Puchta, G.; Schneider, H.; Grosche, M.; Mihalios, D.; Herrmann, W. A. J. Organomet. Chem. 2001, 621, 177-183
85. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652
86. Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206
87. Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789
88. Stephens, P. J.; Devlin, F. J.; Chabalowski, C. F.; Frisch, M. J. J. Phys. Chem. 1994, 98, 11623-11627
89. Andrae, D.; Häußermann, U.; Dolg, M.; Stoll, H.; Preuß, H. Theor. Chim. Acta 1990, 77, 123-141
90. Fukui, K. J. Phys. Chem. 1970, 74, 4161-4163
91. Fukui, K. Acc. Chem. Res. 1981, 14, 363-368
92. Frisch, M. J., Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.