Mechanistic studies on a facile ring-flipping process in planar chiral ferrocenes under ambient and high pressure and its relevance to asymmetric catalysis

Organometallics

Volumn 23, Issue 4, 2004, Pages 906-912

  Curnow, Owen J ^a   Fern, Glen M ^a   Hamilton, Michelle L ^a   Zahl, Achim ^b   Van Eldik, Rudi ^b  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

^b UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CATALYSIS; HIGH PRESSURE EFFECTS; ISOMERIZATION; ISOMERS; SODIUM CHLORIDE; TEMPERATURE;

CHLOROFORM; FERROCENES; RING FLIPPING PROCESS;

ORGANOMETALLICS;

EID: 1542285960     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om030641d     Document Type: Article

References (64)

1. (a) Wagner, G.; Herrmann, R. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.: VCH: Weinheim, Germany, 1995; pp 173-218.
2. (b) Togni, A. In Metallocenes: Synthesis Reactivity Applications; Togni, A., Halterman, R. L., Eds.: Wiley-VCH: Weinheim, Germany, 1998; Vol. 2, pp. 685-722.
3. (c) Hayashi, T. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials Science; Togni, A., Hayashi, T., Eds.; VCH: Weinheim, Germany, 1995; pp 105-142.
4. (d) Togni, A. Angew. Chem., Int. Ed. Engl. 1996, 35, 1475.
5. (e) Dai, L.-X.; Tu, T.; You, S.-L.; Deng, W.-P.; Hou, X.-L. Acc. Chem. Res. 2003, 36, 659.
6. (a) Falk, H.; Lehner, H.; Paul, J.; Wagner, U. J. Organomet. Chem. 1971, 28, 115.
7. (b) Slocum, D. W.; Tucker, S. P.; Engelmann, T. R. Tetrahedron Lett. 1970, 621.
8. (a) Giardello, M. A.; Conticello, V. P.; Brard, L.; Sabat, M; Rheingold, A. L.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10212.
9. (b) Haar, C. M.; Stern, C. L.; Marks, T. J. Organometallics 1996, 15, 1765.
10. (c) Hultzsch, K. C.; Spaniol, T. P.; Okuda, J. Organometallics 1997, 16, 4845.
11. Yoder, J. C.; Day, M. W.; Bercaw, J. E. Organometallics 1998, 17, 4946.
12. (a) Wild, F. R. W. P.; Zsolnai, L.; Huttner, G.; Brintzinger, H. H. J. Organomet. Chem. 1982, 232, 233.
13. (b) Wiesenfeldt, H.; Reinmuth, A.; Barsties, E.; Evertz, K.; Brintzinger, H. H. J. Organomet. Chem. 1989, 369, 359.
14. (c) Schmidt, K.; Reinmuth, A.; Rief, U.; Diebold, J.; Brintzinger, H. H. Organometallics 1997, 16, 1724.
15. (d) Kaminsky, W.; Schauweinold, A.-M.; Freidanck, F. J. Mol. Catal. A 1996, 112, 37.
16. (e) Rheingold, A. L.; Robinson, N. P.; Whelan, J.; Bosnich, B. Organometallics 1992, 11, 1869.
17. (f) Collins, S.; Hong, Y.; Taylor, N. J. Organometallics 1990, 9, 2695.
18. (g) Vitz, E. D.; Wagner, P. J.; Brubaker, C. H., Jr. J. Organomet. Chem. 1976, 107, 301.
19. (h) Ringwald, M.; Stuermer, R.; Brintzinger, H. H. J. Am. Chem. Soc. 1999, 121, 1524.
20. (i) Diamond, G. M.; Rodewald, S.; Jordan, R. F. Organometallics 1995, 14, 5.
21. (j) Christopher, J. N.; Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4038.
22. (k) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4045.
23. (l) Diamond, G. M.; Jordan, R. F.; Petersen, J. L. Organometallics 1996, 15, 4030.
24. (a) Hollis, T. K.; Wang, L.-S.; Tham, F. J. Am. Chem. Soc. 2000, 122, 11737.
25. (b) Bellemin-Laponnaz, S.; Lo, M. M. C.; Peterson, T. H.; Allen, J. M.; Fu, G. C. Organometallics 2001, 20, 3453.
26. (c) Hollis, T. K.; Ahn, Y. J.; Tham, F. S. Chem. Commun. 2002, 2996.
27. (a) Herberich, G. E.; Jansen, U. J. Organometallics 1995, 14, 834.
28. (b) Herberich, G. E.; Dunne, B. J.; Hessner, B. Angew. Chem. 1989, 101, 798.
29. (c) Heberich, G. E.; Bueschges, U.; Dunne, B. J.; Hessner, B.; Klaff, N.; Koeffer, D. P. J.; Peters, K. J. Organomet. Chem. 1989, 372, 53.
30. (d) Herberich, G. E.; Englert, U.; Marken, F.; Hofmann, P. Organometallics 1993, 12, 4039.
31. (a) Bublitz, D. Can. J. Chem. 1964, 42, 2381.
32. (b) Bublitz, D. E. J. Organomet. Chem. 1969, 16, 149.
33. (c) Hayashi, T.; Okada, Y.; Shimizu, S. Transition Met. Chem. 1996, 21, 418.
34. (d) Astruc, D.; Dabard, R. J. Organomet. Chem. 1975, 96, 283.
35. (e) Astruc, D.; Dabard, R. J. Organomet. Chem. 1976, 111, 339.
36. Kudinov, A. R.; Fil'chikov, A. A.; Petrovskii, P. V.; Rybinskaya, M. I. Russ. Chem. Bull. (Engl. Transl.) 1999, 48, 1352.
37. Spradau, T. W.; Katzenellenbogen, J. A. Organometallics 1998, 17, 2009.
38. Allcock, H. R.; McDonnell, G. S.; Riding, G. H.; Manners, I. Chem. Mater. 1990, 2, 425.
39. Gauthier, G. J. Chem. Soc., Chem. Commun. 1969, 690.
40. Adams, J. J.; Berry, D. E.; Browning, J.; Burth, D; Curnow, O. J. J. Organomet. Chem. 1999, 580, 245.
41. Curnow, O. J.; Fern, G. M. Organometallics 2002, 21, 2827.
42. These activation parameters differ slightly from those given in ref 14, which were calculated from an Arrhenius fit.
43. (a) Kakkar, A. K.; Taylor, N. J.; Marder, T. B. Organometallics 1989, 8, 1765.
44. Marder, T. B.; Williams, I. D. J. Chem. Soc., Chem. Commun. 1987, 1478.
45. (a) van Eldik, R.; Asano, T.; le Noble, W. J. Chem. Rev. 1989, 89, 549.
46. (b) Drljaca, A.; Hubbard, C. D.; van Eldik, R.; Asano, T.; Basilevsky, M. V.; le Noble, W. J. Chem. Rev. 1998, 98, 2167.
47. (c) van Eldik, R.; Dücker-Benfer, C.; Thaler, F. Adv. Inorg. Chem. 2000, 49, 1.
48. (d) High-Pressure Chemistry: Synthetic, Mechanism and Supercritical Applications; van Eldik, R. Klärner, F.-G., Eds.: Wiley-VCH: Weinheim, Germany, 2002.
49. Mizuta, T.; Imamura, Y.; Miyoshi, K. J. Am. Chem. Soc. 2003, 125, 2068.
50. (a) Catheline, D.; Astruc, D. Organometallics 1984, 3, 1094.
51. (b) Catheline, D.; Astruc, D. J. Organomet. Chem. 1983, 248, C9.
52. (c) Boyd, D. C.; Bohling, D. A.; Mann, K. R. J. Am. Chem. Soc. 1985, 107, 1641.
53. (d) Gill, T. P.; Mann, K. R. Inorg. Chem. 1980, 19, 3007.
54. (e) Gill, T. P.; Mann, K. R. J. Organomet. Chem. 1981, 216, 65.
55. (f) Gill, T. P.; Mann, K. R. Inorg. Chem. 1983, 22, 1986.
56. (g) Cathaline, D.; Astruc, D. J. Organomet. Chem. 1984, 272, 417.
57. (h) Swann, R. T.; Boekelheide, V. J. Organomet. Chem. 1982, 231, 143.
58. (i) Laganis, E. D.; Finke, R. G.; Boekelheide, V. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 2657.
59. (a) O'Connor, J. M.; Casey, C. P. Chem. Rev. 1987, 87, 307.
60. (b) Cadierno, V.; Diez, J.; Gamasa, M. P.; Gimeno, J.; Lastra, E. Coord. Chem. Rev. 1999, 193-195, 147.
61. (c) Calhorda, M. J.; Felix, V.; Veiros, L. F. Coord. Chem. Rev. 2002, 230, 49.
62. Fallis, K. A.; Anderson, G. K.; Rath, N. P. Organometallics 1992, 11, 885.
63. Zahl, A.; Igel, P.; Weller, M.; van Eldik, R. Manuscript in preparation.
64. Zahl, A.; Neubrand, A.; Aygen, S.; van Eldik, R. Rev. Sci. Instrum. 1994, 65, 882.