Octamethyloctahydrodibenzofluorenyl: Electronic comparisons between a sterically expanded ligand and its cyclopentadienyl analogues

Organometallics

Volumn 27, Issue 15, 2008, Pages 3722-3727

  Price, Craig J ^a   Zeits, Paul D ^a   Reibenspies, Joseph H ^a   Miller, Stephen A ^a,b  

^a TEXAS A AND M UNIVERSITY   (United States)

^b University of Florida   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CONSTRAINED GEOMETRY; CYCLOPENTADIENYL; METALLOCENE; OLEFIN POLYMERIZATION CATALYSTS;

ABS RESINS; CHEMICAL REACTIONS; MONOMERS; OLEFINS; ORGANOMETALLICS; POLYMERS;

CATALYSIS;

EID: 50549091133     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om8001526     Document Type: Article

References (59)

1. For reviews of single-site olefin polymerization, see: (a) Stereoselective Polymerization with Single-Site Catalysts; Baugh, L. S., Canich, J. A. M., Eds.; CRC Press: New York, 2007.
2. (b) Price, C. J.; Aubry, D. A.; Irwin, L. J.; MillerS. A. In Stereoselective Polymerization with Single-Site Catalysts; Baugh, L. S., Canich, J. A. M., Eds.; CRC Press: New York, 2007; pp 37-82.
3. (c) Marks, T. J., Ed. Proc. Natl. Acad. Sci. U.S.A. 2006, 103(42) (Polymerization Special Feature).
4. (d) Severn, J. R.; Chadwick, J. C.; Duchateau, R.; Friederichs, N. Chem. Rev. 2005, 105, 4073-4147.
5. (e) Kaminsky, W. J. Polym. Sci., Part A: Polym. Chem. 2004, 42, 3911-3921.
6. (f) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283-316.
7. (g) LeinoR. In Encyclopedia of Polymer Science and Technology, 3rd ed.; Kroschwitz, J. I., Ed.; Wiley & Sons: New York, 2003.
8. (h) Vlád, G. In Encyclopedia of Catalysis; Horváth, I. T., Ed.; Wiley Interscience: Hoboken, NJ, 2003; Vol. 5, pp 611-737.
9. (i) Gladysz, J. A., Ed. Chem. Rev. 2000, 100(special issue on Frontiers in Metal-Catalyzed Polymerization).
10. (j) Coates, G. W. Chem. Rev. 2000, 100, 1223-1252.
11. (k) Resconi, L.; Cavallo, L.; Fait, A.; Piemontesi, F. Chem. Rev. 2000, 100, 1253-1345.
12. (l) Brintzinger, H.-H.; Fischer, D.; Mülhaupt, R.; Rieger, B.; Waymouth, R. M. Angew. Chem., Int. Ed. 1995, 34, 1143-1170.
13. Scheirs, J., Kaminsky, W., Eds. Metallocene-Based Polyolefins: Preparation, Properties and Technology; John Wiley & Sons: New York, 2000.
14. (b) Patil, A. O., Hlatky, G. G., Eds. Beyond Metallocenes: Next-Generation Polymerization Catalysts; American Chemical Society: Washington, D.C., 2003.
15. (a) Shapiro, P. J.; Bunel, E.; Schaefer, W. P.; Bercaw, J. E. Organometallics 1990, 9, 867-869.
16. (b) Shapiro, P. J.; Cotter, W. D.; Schaefer, W. P.; Labinger, J. A.; Bercaw, J. E. J. Am. Chem. Soc. 1994, 116, 4623-4640.
17. (c) Okuda, J. Chem. Ber. 1990, 123, 1649-1651.
18. (d) Stevens, J. C.; Timmers, F. J.; Wilson, D. R.; Schmidt, G. F.; Nickias, P. N.; Rosen, R. K.; Knight, G. W.; Lai, S. Y. European Patent 416815-A2, 1991.
19. (e) Canich, J. A. M. U.S. Patent 5,026,798, 1991.
20. (f) Turner, H. W.; Hlatky, G. G.; Canich, J. A. M. World Patent 9319103, 1993.
21. (a) Kawai, K.; Yamashita, M.; Tohi, Y.; Kawahara, N.; Michiue, K.; Kaneyoshi, H.; Mori, R. PCT Int. Appl. WO 01/27124, 2001.
22. (b) Miller, S. A.; Bercaw, J. E. U.S. Patent 6,469,188, 2002.
23. (c) Miller, S. A.; Bercaw, J. E. U.S. Patent 6,693,153, 2004.
24. (a) Miller, S. A.; Bercaw, J. E. Organometallics 2004, 23, 1777-1789.
25. (b) Miller, S. A.; Bercaw, J. E. Organometallics 2006, 25, 3576-3592.
26. Irwin, L. J.; Reibenspies, J. H.; Miller, S. A. J. Am. Chem. Soc. 2004, 126, 16716-16717.
27. (a) Irwin, L. J.; Reibenspies, J. H.; Miller, S. A. Polyhedron 2005, 24, 1314-1324.
28. (b) Miller, S. A.; Irwin, L. J. U.S. Patent 7,214,749, 2007.
29. Guilhemat, R.; Pereyre, M.; Pétraud, M. Bull. Soe. Chim. Fr. 1980, 2, 334-344.
30. An extensive study of steric effects in ania-metallocenes has been carried out by Helmut Alt:(a) Schmid, M. A.; Alt, H. G.; Milius, W. J. Organomet. Chem. 1995, 501, 101-106.
31. (b) Alt, H. G.; Zenk, R. J. Organomet. Chem. 1996, 518, 7-15.
32. (c) Alt, H. G.; Zenk, R. J. Organomet. Chem. 1996, 522, 39-54.
33. (d) Schmid, M. A.; Alt, H. G.; Milius, W. J. Organomet. Chem. 1996, 525, 9-14.
34. (e) Schertl, P.; Alt, H. G. J. Organomet. Chem. 1999, 582, 328-337.
35. Irwin, L. J.; Miller, S. A. J. Am. Chem. Soc. 2005, 127, 9972-9973.
36. (a) Möhring, P. C.; Coville, N. J. J. Mol. Catal. 1992, 77, 41-50.
37. (b) Möhring, P. C.; Vlachakis, N.; Grimmer, N. E.; Coville, N. J. J. Organomet. Chem. 1994, 483, 159-166.
38. There have been several reports investigating catalytic behavior of electronically variable catalysts with minimal steric perturbation, including: (a) Piccolrovazzi, N.; Pino, P.; Consiglio, G.; Sironi, A.; Moret, M. Organometallics 1990, 9, 3098-3105.
39. (b) Lee, I.-M.; Gauthier, W. J.; Ball, J. M.; Iyengar, B.; Collins, S. Organometallics 1992, 11, 2115-2122.
40. (c) Ewen, J. A.; Reddy, B. R.; Elder, M. J. U.S. Patent 5,710,222, 1998.
41. Friebolin H. Basic One-and Two-Dimensional NMR Spectroscopy, 2nd ed.; VCH: Weinheim, Germany, 1993; pp 20-21.
42. a of fluorene is reported as 22.6 in DMSO at 25°C: Bordwell, F. G. Acc. Chem. Res. 1988, 21, 456-463.
43. a of fluorene is reported as 22.4 in tetrahydrofuran and is calculated to be 23.0 in water: Streitwieser, A., Jr Acc. Chem. Res. 1984, 17, 353-357.
44. Gau, G.; Marques, S. J. Am. Chem. Soc. 1976, 98, 1538-1541.
45. Irwin, L. J.; Zeits, P. D.; Reibenspies, J. H.; Miller, S. A. Organometallics 2007, 26, 1129-1133.
46. Decken, A.; MacKay, A. J.; Brown, M. J.; Bottomley, F. Organometallics 2002, 21, 2006-2009.
47. Frankcom, T. M.; Green, J. C.; Nagay, A.; Kakkar, A. K.; Marder, T. B. Organometallics 1993, 12, 3688-3697.
48. Zachmanoglou, C. E.; Docrat, A.; Bridgewater, B. M.; Parkin, G.; Brandow, C. G.; Bercaw, J. E.; Jardine, C. N.; Lyall, M.; Green, J. C.; Keister, J. B. J. Am. Chem. Soc. 2002, 124, 9525-9546.
49. King, R. B.; Efraty, A. J. Am. Chem. Soc. 1972, 94, 3773-3779.
50. Ewen, J. A.; Jones, R. L.; Razavi, A.; Ferrara, J. D. J. Am. Chem. Soc. 1988, 110, 6255-6256.
51. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004.
52. Becke, A. D. J. Chem. Phys. 1993, 98, 5648-5652.
53. (a) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. 1988, B37, 785-789.
54. (b) Miehlich, B.; Savin, A.; Stoll, H.; Preuss, H. Chem. Phys. Lett. 1989, 157, 200-206.
55. Petersson, G. A.; Al-Laham, M. A. J. Chem. Phys. 1991, 94, 6081-6090.
56. Dunning, T. H., Jr.; Hay, P. J. In Modern Theoretical Chemistry; Schaefer, H. F., III, Ed.; Plenum: New York, 1976; Vol. 3, pp 1-28.
57. (b) Hay, P. J.; Wadt, W. R. J. Chem. Phys. 1985, 82, 270-283.
58. (a) Krishnan, R.; Binkley, J. S.; Seeger, R.; Pople, J. A. J. Chem. Phys. 1980, 72, 650-654.
59. (b) Spintzagel, G. W.; Clark, T.; Schleyer, P. v. R. J. Comput. Chem. 1987, 8, 1109-1116.