Mechanism of Unlike Stereoselectivity in 1-Alkene Primary Insertions: Syndiospecific Propene Polymerization by Brookhart-Type Nickel(II) Catalysts

Organometallics

Volumn 19, Issue 7, 2000, Pages 1343-1349

  Milano, Giuseppe ^a   Guerra, Gaetano ^a   Pellecchia, Claudio ^a   Cavallo, Luigi ^b  

^a UNIVERSITY OF SALERNO   (Italy)

^b UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000570461     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om990796e     Document Type: Article

References (84)

1. Zambelli, A.; Tosi, C. Adv. Polym. Sci. 1974, 31.
2. Corradini, P.; Busico, V.; Guerra, G. Comprehensive Polymer Science; Allen, G., Bevington, J. C., Eds.; Pergamon Press: Oxford, 1989; Vol. 4, p 29.
3. Bovey, F. A.; Tiers, G. V. D. J. Polym. Sci. 1960, 44, 173.
4. Sheldon, R. A.; Fueno, T.; Tsunetsugu, T.; Furukawa, J. J. Polym. Sci. Part B 1965, 3, 23.
5. Doi, Y.; Asakaru, T. Makromol. Chem. 1975, 176, 507.
6. Zambelli, A.; Ammendola, P. Prog. Polym. Sci. 1991, 16.
7. Natta, G. Nobel Lectures in Chemistry, 1963-1970; Elsevier: New York, 1972; p 27.
8. Ziegler, K. Nobel Lectures in Chemistry, 1963-1970; Elsevier: New York, 1972; p 6.
9. Moore, E. P. J. Polypropylene Handbook: Polymerization, Characterization, Properties, Applications; Hanser Publishers: Munich, 1996.
10. Ewen, J. A. J. Am. Chem. Soc. 1984, 106, 6355.
11. Kaminsky, W.; Külper, K.; Brintzinger, H. H.; Wild, F. R. W. P. Angew. Chem., Int. Ed. Engl. 1985, 24, 507.
12. Ewen, J. A.; Jones, R. L.; Razavi, A.; Ferrara, J. D. J. Am. Chem. Soc. 1988, 110, 6255.
13. Corradini, P.; Barone, V.; Fusco, R.; Guerra, G. Eur. Polym. J. 1979, 15, 133.
14. Corradini, P.; Barone, V.; Guerra, G. Macromolecules 1982, 15, 1242.
15. Corradini, P.; Barone, V.; Fusco, R.; Guerra, G. J. Catal. 1982, 77, 32.
16. Corradini, P.; Guerra, G.; Vacatello, M.; Villani, V. Gazz. Chim. Ital. 1988, 118, 173.
17. Cavallo, L.; Corradini, P.; Guerra, G.; Vacatello, M. Macromolecules 1991, 24, 1784.
18. Castonguay, L. A.; Rappé, A. K. J. Am. Chem. Soc. 1992, 114, 5832.
19. Kawamura-Kuribayashi, H.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1992, 114, 8687.
20. Hart, J. A.; Rappé, A. K. J. Am. Chem. Soc. 1993, 115, 6159.
21. Cavallo, L.; Corradini, P.; Guerra, G.; Vacatello, M. Polymer 1991, 32, 1329.
22. Guerra, G.; Cavallo, L.; Moscardi, G.; Vacatello, M.; Corradini, P. J. Am. Chem. Soc. 1994, 116, 2988.
23. Pietsch, M. A.; Rappé, A. K. J. Am. Chem. Soc. 1996, 118, 10908.
24. Guerra, G.; Cavallo, L.; Moscardi, G.; Vacatello, M.; Corradini, P. Macromolecules 1996, 26, 4834.
25. van der Leek, K.; Angermund, K.; Reffke, M.; Kleinschmidt, R.; Goretzki, R.; Fink, G. Chem. Eur. J. 1997, 3, 58.
26. Corradini, P.; Cavallo, L.; Guerra, G. In Metallocene Based Polyolefins, Preparation, Properties and Technology; Scheirs, J., Kaminsky, W., Eds.; Wiley: Chichester, 2000; Vol. 2, p 3.
27. Longo, P.; Proto, A.; Grassi, A.; Ammendola, P. Macromolecules 1991, 24, 4624.
28. Zambelli, A.; Sacchi, M. C.; Locatelli, P.; Zannoni, G. Macromolecules 1982, 15, 211.
29. Longo, P.; Grassi, A.; Pellecchia, C.; Zambelli, A. Macromolecules 1987, 20, 1015.
30. Cavallo, L.; Guerra, G.; Corradini, P.; Vacatello, M. Chirality 1991, 3, 299.
31. Pino, P.; Cioni, P.; Wei, J. J. Am. Chem. Soc. 1987, 109, 6189.
32. Pino, P.; Galimberti, M.; Prada, P.; Consiglio, G. Makromol. Chem. 1990, 191, 1677.
33. Gilchrist, J. H.; Bercaw, J. E. J. Am. Chem. Soc. 1996, 118, 12021.
34. Toto, M.; Cavallo, L.; Corradini, P.; Guerra, G.; Resconi, L. Macromolecules 1998, 31, 3431.
35. Guerra, G.; Cavallo, L.; Corradini, P.; Longo, P.; Resconi, L. J. Am. Chem. Soc. 1997, 119, 4394.
36. Resconi, L.; Abis, L.; Franciscono, G. Macromolecules 1992, 25, 6814.
37. Erker, G.; Fritze, C. Angew. Chem., Int. Ed. Engl. 1992, 31, 199.
38. Zambelli, A.; Tosi, C.; Sacchi, C. Macromolecules 1972, 5, 649.
39. Zambelli, A.; Locatelli, P.; Rigamonti, E. Macromolecules 1979, 12, 156.
40. Zambelli, A.; Allegra, G. Macromolecules 1980, 13, 42.
41. Ewen, J. A. In Catalytic Polymerization of Olefins; Keii, T., Soga, K., Eds.; Elsevier: New York, 1986; p 271.
42. Zambelli, A.; Ammendola, P.; Grassi, A.; Longo, P.; Proto, A. Macromolecules 1986, 19, 2703.
43. Ammendola, P.; Pellecchia, C.; Longo, P.; Zambelli, A. Gazz. Chim. Ital. 1987, 117, 65.
44. Johnson, L. K.; Killian, C. M.; Brookhart, M. S. J. Am. Chem. Soc. 1995, 117, 6414.
45. Killian, C. M.; Tempi, D. J.; Johnson, L. K.; Brookhart, M. J. Am. Chem. Soc. 1996, 118, 11664.
46. Pellecchia, C.; Zambelli, A.; Oliva, L.; Pappalardo, D. Macromolecules 1996, 29, 6990.
47. Pellecchia, C.; Zambelli, A.; Mazzeo, M.; Pappalardo, D. J. Mol. Catal. A: Chem. 1998, 128, 229.
48. Small, B. L.; Brookhart, M. Polym. Prepr. 1998, 39, 213.
49. Pellecchia, C.; Mazzeo, M.; Pappalardo, D. Macromol. Rapid Commun. 1998, 19, 651.
50. Small, B. L.; Brookhart, M. Macromolecules 1999, 32, 2120.
51. Guerra, G.; Corradini, P.; Pucciariello, R. Macromolecules 1985, 18, 2030.
52. Venditto, V.; Guerra, G.; Corradini, P.; Fusco, R. Polymer 1990, 31, 530.
53. Deng, L.; Woo, T. K.; Cavallo, L.; Margl, P. M.; Ziegler, T. J. Am. Chem. Soc. 1997, 119, 6177.
54. Pellecchia, C.; Zambelli, A. Macromol. Rapid Commun. 1996, 17, 333.
55. Hanson, K. R. J. Am. Chem. Soc. 1966, 88, 2731.
56. Corradini, P.; Guerra, G.; Barone, V. Eur. Polym. J. 1984, 20, 1177.
57. IUPAC Commission of Macromolecular Nomenclature. Pure Appl. Chem. 1979, 51, 1101.
58. ADF 2.3.0 Users Guide; Vrije Universiteit Amsterdam: Amsterdam, The Netherlands, 1996.
59. Baerends, E. J.; Ellis, D. E.; Ros, P. Chem. Phys. 1973, 2, 41.
60. te Velde, B.; Baerends, E. J. J. Comput. Phys. 1992, 99, 84.
61. Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, 1200.
62. Becke, A. Phys. Rev. A 1988, 38, 3098.
63. Perdew, J. P. Phys. Rev. B 1986, 33, 8822.
64. Perdew, J. P. Phys. Rev. B 1986, 34, 7406.
65. Cavallo, L.; Woo, T. K.; Ziegler, T. Can. J. Chem. 1998.
66. Woo, T. K.; Cavallo, L.; Ziegler, T. Theor. Chem. Acc. 1998, 100, 307.
67. Maseras, F.; Morokuma, K. J. Comput. Chem. 1995, 16, 1170.
68. Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M. J. Comput. Chem. 1983, 4, 187.
69. Doman, T. N.; Hollis, T. K.; Bosnicj, B. J. Am. Chem. Soc. 1995, 117, 1352.
70. Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Shiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
71. Margl, P. M.; Woo, T. K.; Ziegler, T. Organometallics 1998, 17, 4997.
72. Margl, P. M.; Ziegler, T. Organometallics 1996, 15, 5519.
73. Margl, P. M.; Ziegler, T. J. Am. Chem. Soc. 1996, 118, 7337.
74. Rix, F. C.; Brookhart, M.; White, P. S. J. Am. Chem. Soc. 1996, 118, 4746-4764.
75. Musaev, D. G.; Froese, R. D. J.; Svensson, M.; Morokuma, K. J. Am. Chem. Soc. 1997, 119, 367.
76. Margl, P. M.; Deng, L.; Ziegler, T. Organometallics 1998, 17, 933.
77. Brookhart, M.; Green, M. L. H.; Wong, L. Prog. Inorg. Chem. 1988, 36, 1.
78. Piers, W. E.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 9406.
79. Kraudelat, H.; Brintzinger, H. H. Angew. Chem., Int. Ed. Engl. 1990, 29, 1412.
80. Lohrenz, J. C. W.; Woo, T. K.; Ziegler, T. J. Am. Chem. Soc. 1998, 117, 12793.
81. Suter, U. V.; Flory, P. J. Macromolecules 1975, 8, 765.
82. Corradini, P. In The Stereochemistry of Macromolecules; Ketley, A. D., Ed.; Marcel Dekker: New York, 1968; Vol. 3, Chapter 1, p 1.
83. Pellecchia, C. Unpublished results.
84. Note Added in Proof: The absence of an olefin coordination complex has been recently confirmed by NMR studies: Svejda, S. A.; Johnson, L. R.; Brookhart, M. J. Am. Chem. Soc. 1999, 121, 10634.