Syndio- and isoselective coordinative chain transfer polymerization of styrene promoted by ansa-lanthanidocene/ dialkylmagnesium systems

Advanced Synthesis and Catalysis

Volumn 353, Issue 8, 2011, Pages 1367-1374

  Sarazin, Yann ^a   De Frémont, Pierre ^a   Annunziata, Liana ^a   Duc, Michel ^b   Carpentier, Jean François ^a  

^a INSTITUT DES SCIENCES CHIMIQUES DE RENNES   (France)

^b TOTAL   (France)

Author keywords

coordinative chain transfer polymerization; dialkylmagnesium; lanthanidocenes; polystyrenes; stereospecificity

Indexed keywords

EID: 79957542003     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201100059     Document Type: Article

References (62)

1. For recent reviews, see
2. A.-S. Rodrigues, E. Kirillov, J.-F. Carpentier, Coord. Chem. Rev. 2008, 252, 2115
3. J. Schellenberg, Prog. Polym. Sci. 2009, 34, 688. For post-metallocene titanium complexes bearing amidinate ligands, see
4. J. C. Flores, J. C. W. Chien, M. D. Rausch, Organometallics 1995, 14, 1927
5. J. C. Flores, J. C. W. Chien, M. D. Rausch, Organometallics 1995, 14, 2106. For titanium complexes with sulfur-bridged bis(phenolate)ligands, see
6. C. Capacchione, A. Proto, H. Ebeling, R. Mülhaupt, K. Moller, T. P. Spaniol, J. Okuda, J. Am. Chem. Soc. 2003, 125, 4964
7. K. Beckerle, R. Manivannan, B. Lian, G.-J. M. Meppelder, G. Raabe, T. P. Spaniol, H. Ebeling, F. Pelascini, R. Mülhaupt, J. Okuda, Angew. Chem. 2007, 119, 4874
8. Angew. Chem. Int. Ed. 2007, 46, 4790
9. G. J. M. Meppelder, K. Beckerle, R. Manivannan, B. Lian, G. Raabe, T. P. Spaniol, J. Okuda, Chem. Asian J. 2008, 3, 1312. For (hemi)metallocene complexes based on lanthanide and group 3 metals, see
10. S. Harder, Angew. Chem. 2004, 116, 2768
11. Angew. Chem. Int. Ed. 2004, 43, 2714
12. Y. Luo, J. Baldamus, Z. Hou, J. Am. Chem. Soc. 2004, 126, 13910
13. F. Jaroschik, T. Shima, X. Li, K. Mori, L. Ricard, X.-F. Le Goff, F. Nief, Z. Hou, Organometallics 2007, 26, 5654
14. P. Zinck, A. Valente, A. Mortreux, M. Visseaux, Polymer 2007, 48, 4609
15. X. Fang, X. Li, Z. Hou, J. Assoud, R. Zhao, Organometallics 2009, 28, 517
16. F. Bonnet, C. Da Costa Violante, P. Roussel, A. Mortreux, M. Visseaux, Chem. Commun. 2009, 3380
17. E. Kirillov, C. W. Lehmann, A. Razavi, J.-F. Carpentier, J. Am. Chem. Soc. 2004, 126, 12240
18. A.-S. Rodrigues, E. Kirillov, C. W. Lehmann, T. Roisnel, B. Vuillemin, A. Razavi, J.-F. Carpentier, Chem. Eur. J. 2007, 13, 5548
19. L. Perrin, Y. Sarazin, E. Kirillov, J-F. Carpentier, L. Maron, Chem. Eur. J. 2009, 15, 2773
20. L. Perrin, E. Kirillov, J.-F. Carpentier, L. Maron, Macromolecules 2010, 43, 6330.
21. N. Ishihara, M. Kuramoto, M. Uoi, (to Idemitsu Kosan Co Ltd), Japanese Patent 62187708, 1985
22. N. Ishihara, T. Seimiya, M. Kuramoto, M. Uoi, Macromolecules 1986, 19, 2464.
23. T. Arai, T. Ohtsu, S. Suzuki, Polym. Prepr. Am. Chem. Soc. Div. Polym. Chem. 1998, 39, 220
24. C. Capacchione, A. Proto, H. Ebeling, R. Mulhaupt, K. Moller, T. P. Spaniol, J. Okuda, J. Am. Chem. Soc. 2003, 125, 4964
25. C. Capacchione, R. Manivannan, M. Barone, K. Beckerle, R. Centore, L. Oliva, A. Proto, A. Tuzi, T. P. Spaniol, J. Okuda, Organometallics 2005, 24, 2971
26. A.-S. Rodrigues, E. Kirillov, T. Roisnel, A. Razavi, B. Vuillemin, J.-F. Carpentier, Angew. Chem. 2007, 119, 7378
27. Angew. Chem. Int. Ed. 2007, 46, 7240.
28. G. Natta, P. Pino, P. Corradini, F. Danusso, E. Mantica, G. Mazzanti, G. Moraglio, J. Am. Chem. Soc. 1955, 77, 1708
29. G. Natta, P. Corradini, Makromol. Chem. 1955, 16, 77
30. M. Rosário Riberio, M. F. Portela, A. Deffieux, H. Cramail, M. F. Rocha, Macromol. Rapid Commun. 1996, 17, 461
31. Q. Sun, Y. Fan, S. Liao, J. Liu, F. Wan, J. Xu, Polymer 2001, 42, 4087
32. G. Xu, S. Lin, Macromol. Rapid Commun. 1994, 15, 873.
33. J. Kern, Nature 1960, 187, 410
34. L. Cazzaniga, R. E. Cohen, Macromolecules 1989, 22, 4125
35. T. Makino, T. E. Hogen-Esch, Macromolecules 1999, 32, 5712.
36. For recent reviews on reversible chain growth polymerization of olefins, see
37. R. Kempe, Chem. Eur. J. 2007, 13, 2764
38. L. R. Sita, Angew. Chem. 2009, 121, 2500
39. Angew. Chem. Int. Ed. 2009, 48, 2464.
40. J.-F. Pelletier, A. Mortreux, X. Olonde, K. Bujadoux, Angew. Chem. 1996, 108, 1980
41. Angew. Chem. Int. Ed. Engl. 1996, 35, 1854
42. T. Chenal, X. Olonde, J.-F. Pelletier, K. Bujadoux, A. Mortreux, Polymer 2007, 48, 1844
43. J. Gromada, T. Chenal, A. Mortreux, J. W. Ziller, F. Leising, J.-F. Carpentier, Chem. Commun. 2000, 2183
44. J. Gromada, A. Mortreux, T. Chenal, J. W. Ziller, F. Leising, J.-F. Carpentier, Chem. Eur. J. 2002, 8, 3773.
45. A.-S. Rodrigues, E. Kirillov, B. Vuillemin, A. Razavi, J.-F. Carpentier, J. Mol. Catal. A 2007, 273, 87.
46. A. Valente, P. Zinck, A. Mortreux, M. Visseaux, Macromol. Rapid Commun. 2009, 30, 528.
47. P. Zinck, A. Valente, A. Mortreux, M. Visseaux, Polymer 2007, 48, 4609
48. P. Zinck, A. Valente, F. Bonnet, A. Violante, A. Mortreux, M. Visseaux, S. Ilinca, R. Duchateau, P. Roussel, J. Polym. Sci. Polym. Chem. Ed. 2010, 48, 802.
49. A. Valente, P. Zinck, M. J. Vitorino, A. Mortreux, M. Visseaux, J. Polym. Sci. Polym. Chem. Ed. 2010, 48, 4640.
50. Z. Jian, D. Cui, Z. Hou, X. Li, Chem. Commun. 2010, 46, 3022.
51. The behaviour of 2 as a single-component catalyst/initiator [i.e., in the absence of added (n-butyl)magnesium] was not investigated in detail. The low apparent activity/productivity observed suggests that the initiation efficiency is quite low, as well as the amount of active species.
52. F. Feil, S. Harder, Macromolecules 2003, 36, 3446.
53. m, see:, V. Busico, R. Cipullo, Prog. Polym. Sci. 2001, 26, 443.
54. L. Annunziata, A.-S. Rodrigues, E. Kirillov, Y. Sarazin, J. Okuda, L. Perrin, L. Maron, J.-F. Carpentier, Macromolecules 2011, 44, 3312-3322.
55. H. J. Harwood, T. K. Chen, F. T. Lin, ACS Symp. Ser. 1984, 247, 197
56. T. K. Chen, H. J. Harwood, Makromol. Chem. Rapid Commun. 1983, 4, 463
57. T. Kawamura, N. Toshima, K. Matsuzaki, Macromol. Rapid Commun. 1994, 15, 479
58. P. Longo, A. Grassi, L. Oliva, P. Ammendola, Makromol. Chem. 1990, 191, 237.
59. L. Annunziata, P. de Frémont, Y. Sarazin, J.-F. Carpentier, M. Duc, (to Total Petrochemicals and University of Rennes 1), Eur. Pat. Appl. 10 290620.3.
60. S. C. Watson, J. F. Eastham, J. Organomet. Chem. 1967, 9, 165.
61. T. J. Woodman, M. Schormann, M. Bochmann, Isr. J. Chem. 2002, 42, 283.
62. E. Kirillov, C. W. Lehmann, A. Razavi, J.-F. Carpentier, Organometallics 2004, 23, 2768.