Effect of the alkali-metal cation on the bonding mode of 2,5-dimethylpyrrole in divalent samarium and ytterbium complexes

Organometallics

Volumn 21, Issue 8, 2002, Pages 1707-1713

  Ganesan, Mani ^a   Bérubé, Christian D ^a   Gambarotta, Sandro ^a   Yap, Glenn P A ^a  

^a UNIVERSITY OF OTTAWA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS;

ALKALI METALS; CHEMICAL BONDS; COMPLEXATION; HYDROGEN; POSITIVE IONS; REDUCTION; SAMARIUM COMPOUNDS; SUBSTRATES; SYNTHESIS (CHEMICAL); YTTERBIUM COMPOUNDS;

ORGANOMETALLICS;

EID: 0038002448     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0109915     Document Type: Article

References (76)

1. (a) Molander, G. A.; Hoberg, J. O. J. Org. Chem. 1992, 57, 3266.
2. (b) Jeske, G.; Jauke, H.; Mauermann, H.; Shumann, H.; Marks, T. J. J. Am. Chem. Soc. 1988, 107, 8111.
3. (c) Evans, W. J.; Bloom, I.; Hunter, W. E.; Atwood, J. L. J. Am. Chem. Soc. 1988, 105, 1401.
4. (a) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 9295.
5. (b) Li, Y.; Marks, T. J. Organometallics 1996, 15, 3770.
6. (c) Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1996, 118, 707.
7. (d) Gagné, M. R.; Nolan, S. P.; Marks, T. J. Organometollics 1990, 9, 1716.
8. (a) Fu, P. F.; Brard, L.; Li, Y.; Marks, T. J. J. Am. Chem. Soc. 1995, 117, 7157 and references cited therein.
9. (b) Molander, G. A.; Julius, M. J. Org. Chem. 1992, 57, 6347.
10. (a) Bijpost, E. A.; Duchateau, R.; Teuben, J. H. J. Mol. Catal. 1995, 95, 121.
11. (b) Harrison, K. N.; Marks, T. J. J. Am. Chem. Soc. 1992, 114, 9220.
12. (c) Molander, G. A.; Hoberg, J. O. J. Am. Chem. Soc. 1992, 114, 3123.
13. (a) Thompson, M. E.; Bercaw, J. E. Pure Appl. Chem. 1984, 56, 1.
14. (b) Watson, P. L. J. Am. Chem. Soc. 1982, 104, 337.
15. (c) Parkin, G.; Bunel, E.; Burger, B. J.; Trimmer, M. S.; van Asselt, A.; Bercaw, J. E. J. Mol. Catal. 1987, 41, 21.
16. (d) Watson, P. L.; Roe, D. C. J. Am. Chem. Soc. 1982, 104, 6471.
17. (a) Molander, G. A.; Nichols, P. J. J. Am. Chem. Soc. 1995, 117, 4415.
18. (b) Heeres, H. J.; Heeres, A.; Teuben, J. H. Organometallics 1990, 9, 1508.
19. (c) Piers, W. E.; Bercaw, J. E. J. Am. Chem. Soc. 1990, 112, 9406.
20. (d) Piers, W. E.; Shapiro, P. J.; Bunel, E. E.; Bercaw, J. E. Synlett 1190, 74.
21. (e) Qian, C.; Ge, Y.; Deng, D.; Gu, Y.; Zhang, C. J. Organomet. Chem. 1988, 344, 175.
22. (f) Qian, C.; Zhu, D.; Li, D. J. Organomet. Chem. 1992, 430, 175.
23. See for example: (a) Marks, T. J.; Fragala, I. L. Fundamental and Technological Aspects of Organo-f-Element Chemistry; D. Reidel: Dordrecht, The Netherlands, 1985;
24. (b) Schumann, H. Angew. Chem., Int. Ed. Engl. 1984, 23, 474.
25. (c) Evans, W. J. Polyhedron 1987, 6, 803.
26. (d) Evans, W. J. J. Organomet. Chem. 1983, 250, 217.
27. Evans, W. J.; Allen, N. T.; Ziller, J. W. J. Am. Chem. Soc. 2001, 123, 7927.
28. (a) Jeske, G.; Lauke, H.; Mauermann, H.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8091.
29. (b) Jeske, G.; Schock, L. E.; Swepston, P. N.; Schumann, H.; Marks, T. J. J. Am. Chem. Soc. 1985, 107, 8103.
30. (c) Watson, P. L.; Parshall, G. W. Acc. Chem. Res. 1985, 18, 51.
31. (a) Schumann, H.; Meese-Marktscheffel, J. A.; Esser, L. Chem. Rev. 1995, 95, 865.
32. (b) Edelmann, F. T. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 4, Chapter 2 and references therein.
33. (c) Schaverien, C. J. Adv. Organomet. Chem. 1994, 36, 283 and references therein.
34. (d) Evans, W. J. Adv. Organomet. Chem. 1985, 24, 31 and references therein.
35. (e) Kagan, H. B.; Namy, J. L. In Handbook on the Physics and Chemistry of Rare Earths; Gscgneider, K. A., Eyring, L.; Elsevier; Amsterdam, 1984; Chapter 50.
36. Marks, T. J.; Ernst, R. D. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon Press: Oxford, U.K., 1982; Chapter 21, and references therein.
37. Evans, W. J.; Ulibarri, T. A.; Ziller, J. M. J. Am. Chem. Soc. 1988, 110, 6877.
38. (a) Evans, W. J.; Keyer, R. A.; Rabe, G. W.; Drummond, D. K.; Ziller, J. W. Organometallics 1993, 12, 4664.
39. (b) Evans, W. J.; Grate, J. W.; Doedens, R. J. J. Am. Chem. Soc. 1985, 107, 1671.
40. (c) Evans, W. J.; Ulibarri, T. A. J. Am. Chem. Soc. 1987, 109, 4292.
41. (d) Evans, W. J.; Drummond, D. K. J. Am. Chem. Soc. 1988, 110, 2772.
42. (e) Evans, W. J.; Drummond, D. K. Organometallics 1988, 7, 797.
43. (f) Evans, W. J.; Drummond, D. K.; Chamberlain, L. R.; Doedens, R. J.; Bott, S. G.; Zhang, H.; Atwood, J. L. J. Am. Chem. Soc. 1988, 110, 4983.
44. (g) Evans, W. J.; Drummond, D. K. J. Am. Chem. Soc. 1986, 108, 7440.
45. (h) Evans, W. J.; Ulibarri, T. A.; Ziller, J. W. J. Am. Chem. Soc. 1990, 112, 2314.
46. (i) Evans, W. J.; Grate, J. W.; Hughes, L. A.; Zhang, H.; Atwood, J. L. J. Am. Chem. Soc. 1985, 107, 3728.
47. (a) Sen, A.; Chebolu, V.; Rheingold, A. L. Inorg. Chem. 1987, 26, 1821.
48. (b) Evans, W. J.; Anwander, R.; Ansari, M. A.; Ziller, J. W. Inorg. Chem. 1995, 34, 5.
49. (c) Hitchcock, P. B.; Holmes, S. A.; Lappert, M. F.; Tian, S. J. Chem. Soc., Chem. Commun. 1994, 2691.
50. (d) Biagini, P.; Lugli, G.; Abis, L.; Millini, R. J. Organomet. Chem. 1994, 474.
51. (e) Desurmont, G.; Li, Y.; Yasuda, H.; Maruo, T.; Kanehisa, N.; Kai, Y. Organometallics 2000, 19, 1811.
52. (a) Chebolu, V.; Whittle, R. R.; Sen, A. Inorg. Chem. 1985, 24, 3082.
53. (b) Evans, W. J.; Drummond, D. K.; Zhang, H.; Atwood, J. L. Inorg. Chem. 1988, 27, 575.
54. (c) Evans, W. J.: Rabe, G. W.; Ziller, J. W.; Inorg. Chem. 1994, 33, 3072.
55. (d) White, J. P., III; Deng, H.; Boyd, E. P.; Gallucci, J.; Shore, S. G. Inorg. Chem. 1994, 33, 1685.
56. (e) Evans, W. J.; Rabe, G. W.; Ziller, J. W. Organometallics 1994, 13, 1641.
57. (f) Minhas, R.; Song, J.; Ma, Y.; Gambarotta, S. Inorg. Chem. 1996, 35, 1866.
58. (g) Evans, J. W.; Ansari, M. A.; Ziller, J. W. Inorg. Chem. 1996, 35, 5435.
59. (h) Schaverien, C. J.; Orpen, A. G. Inorg. Chem. 1991, 30, 4968.
60. (i) Edelmann, F. T. Coord. Chem. Rev. 1995, 737, 403.
61. (j) Schumann, H.; Rosenthal, E. C. E.; Winterfield, J.; Kociok-Kohn, G. J. Organomet. Chem. 1995, 495, C12.
62. (a) Nief, F.; Ricard, L. J. Organomet. Chem. 1994, 464, 149.
63. (b) Rabe, G.; Riede, J.; Schier, A. Inorg. Chem. 1996, 35, 2680.
64. (c) Gosink, H. J.; Nief, F.; Ricard, L.; Mathey, F. Inorg. Chem. 1995, 34, 1306.
65. (d) Fryzuk, M. D.; Haddad, T. S.; Rettig, S. J. Organometallics 1992, 11, 2967.
66. (a) Takats, J. J. Alloys Compd. 1997, 249, 52;
67. (b) Hasinoff, L.; Takats, J.; Zhang, X. W.; Bond, A. H.; Rogers, R. D. J. Am. Chem. Soc. 1994, 116, 8833.
68. (c) Ferrence, G. M.; McDonald, R.; Takats, J. Angew. Chem., Int. Ed. 1999, 38, 2233.
69. Ganesan, M.; Gambarotta, S.; Yap, G. P. A. Angew. Chem., Int. Ed. Engl. 2001, 113, 788.
70. Dubé, T.; Conoci, S.; Gambarotta, S.; Yap, G. P. A.; Vasapollo, G. Angew. Chem., Int. Ed. 1999, 38, 3657.
71. Evans, W. J.; Grate, J. W.; Choi, H. W.; Bloom, I.; Hunter, W. E.; Atwood, J. L. J. Am. Chem. Soc. 1985, 107, 941.
72. 3 was prepared by following a standard procedure: (a) Freeman, J. H.; Smith, M. L. J. Inorg. Nucl. Chem. 1958, 7, 224.
73. This compound was transformed into the corresponding tetrahydrofuranate: (b) Manzer, L. E., Inorg. Synth. 1982, 21, 135.
74. Watson, P. L.; Tulip, T. H.; Williams, I. Organometallics 1990, 9, 1999.
75. Angelici, R. J. Inorg. Synth. 1990, 27, 136.
76. Blessing, R. Acta Crystallogr. 1995, A51, 33-38.