Catalytic trimerization of ethene with highly active cyclopentadienyl-arene titanium catalysts

Organometallics

Volumn 21, Issue 23, 2002, Pages 5122-5135

  Deckers, Patrick J W ^a   Hessen, Bart ^a   Teuben, Jan H ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

COCATALYSTS;

CATALYSIS; STABILITY; SUBSTRATES; TITANIUM;

CHEMICAL REACTIONS;

EID: 0038236637     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020765a     Document Type: Article

References (75)

1. Vogt, D. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, Germany, 1996; p 245.
2. Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis; Wiley: New York, 1992; p 56.
3. For examples, see: (a) Skupinska, J. Chem. Rev. 1991, 91, 613.
4. (b) Mecking, S. Coord. Chem. Rev. 2000, 203, 325.
5. (c) Keim, W.; Kowaldt, F. H.; Goddard, R.; Krüger, C. Angew. Chem., Int. Ed. Engl. 1978, 17, 466.
6. (d) Keim, W.; Schulz, R. P. J. Mol. Catal. 1994, 92, 21.
7. (e) Svejda, S. A.; Brookhart, M. Organometallics 1999, 18, 65.
8. (f) Killian, C. M.; Johnson, L. K.; Brookhart, M. Organometallics 1997, 16, 2005.
9. (g) Britovsek, G. J. P.; Mastroianni, S.; Solan, G. A.; Baugh, S. P. D.; Redshaw, C.; Gibson, V. C.; White, A. J. P.; Williams, D. J.; Elsegood, M. R. J. Chem. Eur. J. 2000, 6, 2221.
10. For examples of ethene (and α-olefin) dimerization, see: (a) Muthukumaru Pillai, S.; Ravindranathan, M.; Sivaram, S. Chem. Rev. 1986, 86, 353.
11. (b) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis; Wiley: New York, 1992; p 72.
12. (c) Chauvin, Y.; Olivier, H. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Herrmann, W. A., Eds.; VCH: Weinheim, Germany, 1996; p 258.
13. (d) Britovsek, G. J. P.; Keim, W.; Mecking, S.; Sainz, D.; Wagner, T. J. Chem. Soc., Chem. Commun. 1993, 1632.
14. (e) Christoffers, J.; Bergman, R. G. Inorg. Chim. Acta 1998, 270, 20.
15. (f) Piers, W. E.; Shapiro, P. J.; Bunel, E. E.; Bercaw, J. E. Synlett 1990, 74.
16. (g) Hauptman, E.; Sabo-Etienne, S.; White, P. S.; Brookhart, M.; Garner, J. M.; Fagan, P. J.; Calabrese, J. C. J. Am. Chem. Soc. 1994, 116, 8038.
17. (a) Briggs, J. R. U.S. Pat. Appl. 4668838, 1987.
18. (b) Karol, F. J.; Levine, I. J. U.S. Pat. Appl. 4777315, 1988.
19. (c) Reagan, W. K.; Conroy, B. K. Eur. Pat. Appl. EP-416304, 1990
20. (d) Reagan, W. K.; Conroy, B. K. U.S. Pat. Appl. 5198563, 1993.
21. (e) Tamura, M.; Uchida, K.; Iwanaga, K.; Ito, Y. Eur. Pat. Appl. EP-699648, 1995.
22. (f) Reagan, W. K.; Pettijohn, T. M.; Freeman, J. W. U.S. Pat. Appl. 5523507, 1996.
23. (g) Araki, Y.; Nakamura, H.; Nanba, Y.; Okano, T. U.S. Pat. Appl. 5856612, 1997.
24. (h) Wu, F.-J. U.S. Pat. Appl. 5744677, 1998.
25. (i) Wu, F.-J. U.S. Pat. Appl. 5968866, 1999.
26. (j) Wass, D. F. PCT Int. Appl. WO 0204119, 2002.
27. Carter, A.; Cohen, S. A.; Cooley, N. A.; Murphy, A.; Scutt, J.; Wass, D. F. Chem. Commun. 2002, 858.
28. Romano, A. M.; Proto, A.; Santi, R.; Sommazzi, A.; Grande, M.; Masi, F. PCT Int. Appl. WO 0168572, 2001.
29. Andes, C.; Harkins, S. B.; Murtuza, S.; Oyler, K.; Sen, A. J. Am. Chem. Soc. 2001, 123, 7423.
30. Deckers, P. J. W.; Hessen, B.; Teuben, J. H. Angew. Chem., Int. Ed. 2001, 40, 2516.
31. (a) Sassmannahausen, J.; Powell, A. K.; Anson, C. E.; Wocadlo, S.; Bochmann, M. J. Organomet. Chem. 1999, 592, 84.
32. (b) Longo, P.; Amendola, A. G.; Fortunato, E.; Boccia, A. C.; Zambelli, A. Macromol. Rapid Commun. 2001, 22, 339.
33. (c) Schwecke, C.; Kaminsky, W. J. Polym. Sci. A: Polym. Chem. 2001, 39, 2805.
34. (d) Flores, J. C.; Wood, J. S.; Chien, J. C. W.; Rausch, M. D. Organometallics 1996, 15, 4944.
35. Deckers, P. J. W.; Van der Linden, A. J.; Meetsma, A.; Hessen, B. Eur. J. Inorg. Chem. 2000, 929.
36. Bochmann, M. J. Chem. Soc., Dalton Trans. 1996, 255.
37. Renaut, P.; Tainturier, G.; Gautheron, B. J. Organomet. Chem. 1978, 148, 35.
38. Erker, G.; Aul, R. Chem. Ber. 1991, 124, 1301.
39. Erker, G.; Nolte, R.; Aul, R.; Wilker, S.; Krüger, C.; Noe, R. J. Am. Chem. Soc. 1991, 113, 7594.
40. 10 fraction was 3.8 g, including some residual toluene solvent and cyclooctane standard, as seen by NMR.
41. Karol, F. J. CHEMTECH 1983, 222.
42. Pellecchia, C.; Pappalardo, D.; Gruter, G. J. Macromolecules 1999, 32, 4491.
43. Gillis, D. J.; Tudoret, M. J.; Baird, M. C. J. Am. Chem. Soc. 1993, 115, 2543.
44. Briggs, J. R. J. Chem. Soc., Chem. Commun. 1989, 674.
45. Emrich, R.; Heinemann, O.; Jolly, P. W.; Krüger, C.; Verhovnik, G. P. J. Organometallics 1997, 16, 1511.
46. (a) Thorn, M. G.; Hill, J. E.; Waratuke, S. A.; Johnson, E. S.; Fanwick, P. E.; Rothwell, I. P. J. Am. Chem. Soc. 1997, 119, 8630.
47. (b) Waratuke, S. A.; Thorn, M. G.; Fanwick, P. E.; Rothwell, A. P.; Rothwell, I. P. J. Am. Chem. Soc. 1999, 121, 9111.
48. (a) Manyik, R. M.; Walker, W. E.; Wilson, T. P. J. Catal. 1977, 47, 197.
49. (b) Yang, Y.; Kim, H.; Lee, J.; Paik, H.; Jang, H. G. Appl. Catal. A: Gen. 2000, 193, 29.
50. (a) Köhn, R. D.; Haufe, M.; Kociok-Köhn, G.; Grimm, S.; Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 4337.
51. (b) Mihan, S.; Lilge, D.; Maas, H.; Molnar, F.; Köhn, R.; Seifert, G.; Kociok-Köhn, G. Abstracts of Papers, 221st National Meeting of the American Chemical Society, San Diego, CA, April 2001; American Chemical Society: Washington, DC, 2001; INOR 114.
52. Zhu, F.; Huang, Y.; Yang, Y.; Lin, S. J. Polym. Sci. A: Polym. Chem. 2000, 38, 4258.
53. For examples, see: (a) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015.
54. (b) Bochmann, M.; Lancaster, S. J. Organometallics 1994, 13, 2235.
55. (c) LaPointe, R. E.; Stevens, J. C.; Nickias, P. N.; Mark, M. H. Eur. Pat. Appl. EP-520732-A, 1992.
56. For recent reviews, see: (d) Piers, W. E.; Chivers, T. Chem. Soc. Rev. 1997, 26, 345.
57. (e) Chen, E. Y. X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
58. (a) Bochmann, M.; Green, M. L. H.; Powell, A. K.; Sassmannshausen, J.; Triller, M. U.; Wocadlo, S. J. Chem. Soc., Dalton Trans. 1999, 43.
59. (b) Doerrer, L. H.; Green, M. L. H.; Haüssinger, D.; Sassmannshausen, J. J. Chem. Soc., Dalton Trans. 1999, 2111.
60. 2-bridged species. See: Alt, H. G.; Köppl, A. Chem. Rev. 2000, 100, 1205.
61. CRC Handbook of Chemistry and Physics, 80th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1999; pp 12-14.
62. 2 (X = C, Si) a difference of 6.3° is observed in the respective bend angles. See: (a) Koch, T.; Blaurock, S.; Somoza, F. B., Jr.; Voigt, A.; Kirmse, R.; Hey-Hawkins, E. Organometallics 2000, 19, 2556.
63. (b) Bajgur, C. S.; Tikkanen, W. R.; Petersen, J. L. Inorg. Chem. 1985, 24, 2539.
64. 10.
65. For examples of backbone substituent effects in ansa-metallocenes, see: (a) Razavi, A.; Atwood, J. L. Macromol. Symp. 1995, 89, 345.
66. (b) Alt, H. G.; Zenk, R. J. Organomet. Chem. 1996, 526, 295.
67. (c) Ewen, J. A.; Hapseslagh, L.; Atwood, J. L.; Zhang, H. J. Am. Chem. Soc. 1987, 109, 6544.
68. + cations. See: Pellecchia, C.; Pappalardo, D.; Oliva, L.; Mazzeo, M.; Gruter, G. J. Macromolecules 2000, 33, 2807.
69. For example, see: Murtuza, S.; Harkins, S. B.; Long, G. S.; Sen, A. J. Am. Chem. Soc. 2000, 122, 1867 and references therein.
70. Sassmannshausen, J. Organometallics 2000, 19, 482.
71. Gutmann, S.; Burger, P.; Hund, H. U.; Hofmann, J.; Brintzinger, H. H. J. Organomet. Chem. 1989, 369, 343.
72. Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 2, 245.
73. (b) Massey, A. G.; Park, A. J. J. Organomet. Chem. 1966, 5, 218.
74. Stone, K. J.; Little, R. D. J. Org. Chem. 1984, 49, 1849.
75. Hart, S. L.; Duncalf, D. J.; Hastings, J. J.; McCamley, A.; Taylor, P. C. J. Chem. Soc. Dalton Trans. 1996, 2843.