Octa- and nonamethylfluorene and an electron-rich permethylfluorenyl ruthenocene derivative

Organometallics

Volumn 25, Issue 18, 2006, Pages 4286-4291

  Bazinet, Patrick ^c   Tupper, Karl A ^c   Tilley, T Don ^a,b  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b LAWRENCE BERKELEY NATIONAL LABORATORY   (United States)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

FLUORENYL RUTHENOCENES; LOW POTENTIAL; METHYLATED FLUORENE DERIVATIVES; MIXED LIGAND RUTHENOCENES;

ELECTROCHEMISTRY; METHANOL; MOLECULAR STRUCTURE; OXIDATION; POTENTIAL ENERGY; RATE CONSTANTS; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION;

DERIVATIVES;

EID: 33748567217     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0603464     Document Type: Article

References (57)

1. For reviews On the application of highly substituted cyclopentadienyl ligands, see: (a) Janiak, C.; Schumann, H. Adv. Organomet. Chem. 1991, 33, 291.
2. (b) Okuda, J. Top. Curr. Chem. 1991, 160, 97.
3. 2Ti]: Bercaw, J. E.; Marvich, R. H.; Bell, L. G.; Brintzinger, H. H. J. Am. Chem. Sac. 1972, 94, 1219.
4. 2: Manriquez, J. M.; Bercaw, J. E. J. Am. Chem. Soc. 1974, 96, 6229.
5. 2 (M = U, Th): Manriquez, J. M.; Fagan, P. J.; Marks, T. J. J. Am. Chem. Soc. 1978, 100, 3939.
6. 2]: van Asselt, A.; Burger, B. J.; Gibson, V. C.; Bercaw, J. E. J. Am. Chem. Soc. 1986, 108, 5347.
7. 2Ln (Ln = Sm): Evans, W. J.; Hughes, L. A.; Hanusa, T. P. J. Am. Chem. Soc. 1984, 106, 4270.
8. 2Ln (Ln = Eu, Yb): Andersen, R. A.; Boncella, J. M.; Burns, C. J.; Green, J. C.; Hohl, D.; Rösch, N. J. Chem. Soc., Chem. Commun. 1986, 405.
9. (g) Cp*ZnZnCp*: Resa, I.; Carmona, E.; Gutierrez-Puebla, E.; Monge, A. Science 2004, 305, 1136.
10. For a recent review on Cp* main-group chemistry, see: Jutzi, P.; Reumann, G. J. Chem. Soc., Dalton Trans. 2000, 2237.
11. (a) Rerek, M. E.; Ji, L.-N.; Basolo, F. J. Chem. Soc., Chem. Commun. 1983, 1208.
12. (b) O'Connor, J. M.; Casey, C. P. Chem. Rev. 1987, 87, 307.
13. (c) Westcott, S. A.; Kakkar, A. K.; Stringer, G.; Taylor, N. J.; Marder, T. B. J. Organomet. Chem. 1990, 394, 111.
14. (d) Calhorda, M. J.; Veiros, L. F. J. Organomet. Chem. 2001, 635, 197.
15. (e) Calhorda, M. J.; Romão, C. C.; Veiros, L. F. Chem. Eur. J. 2002, 8, 868.
16. (f) For a review on indenyl complexes of group 8 metals see: Cadierno, V.; Díez, J.; Gamasa, M. P.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 193-195, 147.
17. (g) For a review on indenyl complexes of group 10 metals see: Zargarian, D. Coord. Chem. Rev. 2002, 233-234, 157.
18. For reviews on early-transition-metal fluorenyl compounds see: (a) Kirillov, E.; Saillard, J.-Y.; Carpentier, J.-F. Coord. Chem. Rev. 2005, 249, 1221.
19. (b) Alt, H. G.; Samuel, E. Chem. Soc. Rev. 1998, 27, 323.
20. Examples of late-transition-metal fluorenyl complexes exhibiting varied coordination modes include: (a) Young, K. M.; Miller, T. M.; Wrighton, M. S. J. Am. Chem. Soc. 1990, 112, 1529.
21. (b) Ji, L.-N.; Rerek, M. E.; Basolo, F. Organometallics 1984, 3, 740.
22. (c) Treichel, P. M.; Fivizzani, K. P.; Haller, K. J. Organometallics 1982, 1, 931.
23. (d) Treichel, P. M.; Johnson, J. W. Inorg. Chem. 1977, 16, 749.
24. (e) Johnson, J. W.; Treichel, P. M. J. Chem. Soc., Chem. Commun. 1976, 688.
25. Miyamoto, T. K.; Tsutsui, M.; Chen, L.-B. Chem. Lett. 1981, 729.
26. For examples see: (a) Rerek, M. E.; Basolo, F. J. Am. Chem. Soc. 1984, 106, 5908.
27. (b) Kakkar, A. K.; Jones, S. F.; Taylor, N. J.; Collins, S.; Marder, T. B. J. Chem. Soc., Chem. Commun. 1989, 1454.
28. (c) Kakkar, A. K.; Taylor, N. J.; Marder, T. B.; Shen, J. K.; Hallinan, N.; Basolo, F. Inorg. Chim. Acta 1992, 198-200, 219.
29. (d) Kakkar, A. K.; Stringer, G.; Taylor, N. J.; Marder, T. B. Can. J. Chem. 1995, 73,981.
30. (e) Mantovani, L.; Ceccon, A.; Gambaro, A.; Santi, S.; Ganis, P.; Venzo, A. Organometallics 1997, 16, 2682.
31. (f) Haynes, A.; Haslam, C. E.; Bonnington, K. J.; Parish, L.; Adams, H.; Spey, S. E.; Marder, T. B.; Coventry, D. N. Organometallics 2004, 23, 5907.
32. (g) Gavenonis. J.; Tilley, T. D. J. Organomet. Chem. 2004, 689, 870.
33. (a) O'Hare, D.; Green, J. C.; Marder, T.; Collins, S.; Stringer, G.; Kakkar, A. K.; Kaltsoyannis, N.; Kuhn, A.; Lewis, R.; Mehnert, C.; Scott. P.; Kurmoo, M.; Pugh, S. Organametallics 1992, 11, 48.
34. (b) O'Hare, D.; Murphy, V. J.; Kaltsoyannis, N. J. Chem. Soc., Dalton Trans. 1993, 383.
35. Smith, L. I.; Moyle, C. L. J. Am. Chem. Soc. 1933, 55, 1676.
36. (a) de la Mare, P. B. D.; Johnson, E. A.; Lomas, J. S. J. Chem. Soc. 1965, 6893.
37. (b) Hart, H.; Teuerstein, A. Synthesis 1979, 9, 693.
38. (a) Marks, V.; Gottlieb, H. E.; Melman, A.; Byk, G.; Cohen, S.; Biali, S. E. J. Org. Chem. 2001, 66, 6711.
39. (b) Tong, L.; Lau, H.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1998, 120, 6000.
40. (c) Nishinaga, T.; Inoue, R.; Matsuura, A.; Komatsu, K. Org. Lett. 2002, 4, 4117.
41. (d) Eichler, B. E.; Miracle, G. E.; Powell, D. R.; West, R. Main Group Met. Chem. 1999, 22, 147.
42. The related Cp*(Flu)Ru has been reported in: (a) Gussman, P. G.; Winter, C. H. J. Am. Chem. Soc. 1988, 110, 6130.
43. (b) Kudinov, A. R.; Shul'pina, L. S.; Petrovskii, P. V.; Rybinskaya, M. I. Metalloorg. Khim. 1990, 3, 1391.
44. Examples of other ruthenium fluorenyl compounds include: (a) Buchmeiser, M.; Schottenberger, H. Organometallics 1993, 12, 2472.
45. (b) Wheeler, D. E.; Bitterwolf, T. E. Inorg. Chim. Acta 1993, 205, 123.
46. (c) Yang, J.; Jones, W. M.; Dixon, J. K.; Allison, N. T. J. Am. Chem. Soc. 1995, 117, 9776.
47. (d) Lau, C. S.-W.; Wong, W.-T. J. Chem. Soc., Dalton Trans. 1999, 607.
48. (e) Sun, Y.; Chan, H.-S.; Dixneuf, P. H.; Xie, Z. Organometallics 2004, 23, 5864.
49. The structure of the related compound Cp*(Flu)Os was reported in: Arachchige, S. M.; Heeg, M. J.; Winter, C. H. J. Organomet. Chem. 2005, 690, 4356.
50. Gassman, P. G.; Sowa, J. R., Jr.; Hill, M. G.; Mann, K. R. Organometallics 1995, 14, 4879.
51. Ryan, M. F.; Siedle, A. R.; Burk, M. J.; Richardson, D. E. Organometallics 1992, 11, 4231.
52. Related group 8 ansa-metallocene dications have been isolated for Ru: (a) Hashidzume, K.; Tobita, H.; Ogino, H. Organometallics 1995, 14, 1187.
53. And for Fe: (b) Ogino, H.; Tobita, H.; Habazaki, H.; Shimoi, M. J. Chem. Soc., Chem. Commun. 1989, 828.
54. Hill, M. G.; Lamanna, W. M.; Mann, K. R. Inorg. Chem. 1991, 30, 4687.
55. Connolly, J. W.; Urry. G. Inorg. Chem. 1963, 2, 645.
56. Koelle, U.; Kossakowski, J. Inorg. Synth. 1992, 29, 225.
57. Fagan, P. J.; Ward, M. D.; Calabrese, J. C. J. Am. Chem. Soc. 1989. 111, 1698.