Induction of atropisomeric chirality on heavily substituted phosphametallocenes

Organometallics

Volumn 22, Issue 8, 2003, Pages 1783-1786

  Ogasawara, Masamichi ^a   Yoshida, Kazuhiro ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ATROPISOMERIC CHIRALITY; MONOPHOSPHAMETALLOCENE; PHOSPHAMETALLOCENE;

COMPLEXATION; MIXTURES; MOLECULAR DYNAMICS; MOLECULAR ORIENTATION; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SOLUTIONS; TOLUENE;

IRON COMPOUNDS;

EID: 0037667746     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020835d     Document Type: Article

References (40)

1. (a) Janiak, C.; Schumann, H. Adv. Organomet. Chem. 1991, 33, 291.
2. (b) Okuda, J. Top. Curr. Chem. 1992, 160, 97.
3. (a) Holm, C. H.; Ibers, J. A. J. Chem. Phys. 1959, 30, 885.
4. (b) Mulay, L. N.; Attalla, A. J. Am. Chem. Soc. 1963, 85, 702.
5. (c) Makova, M. K.; Leonova, E. V.; Karimov, Y. S.; Kochetkova, N. S. J. Organomet. Chem. 1973, 55, 185.
6. Luke, W. D.; Streitwieser, A., Jr. J. Am. Chem. Soc. 1981, 103, 3241.
7. (a) Okuda, J.; Herdtweck, E. Chem. Ber. 1988, 121, 1899.
8. (b) Sitzmann, H. J. Organomet. Chem. 1988, 354, 203.
9. (c) Okuda, J. J. Organomet. Chem. 1988, 356, C43.
10. (d) Okuda, J. Chem. Ber. 1989, 122, 1075.
11. (e) Okuda, J. J. Organomet. Chem. 1990, 385, C39.
12. (f) Winter, C. H.; Dobbs, D. A.; Zhou, X.-X. J. Organomet. Chem. 1991, 403, 145.
13. (g) Abel, E. W.; Long, N. J.; Orrell, K. G.; Osborne, A. G.; Sik, V. J. Organomet. Chem. 1991, 403, 195.
14. (h) Kuhn, N.; Jandral, K.; Stubenrauch, S.; Mynott, R. Inorg. Chim. Acta 1993, 206, 1.
15. (i) Hitchcock, P. B.; Nixon, J. F.; Matos, R. M. J. Organomet. Chem. 1995, 490, 155.
16. (j) Black, S. J.; Francis, M. D.; Jones, C. J. Chem. Soc., Dalton Trans. 1997, 2183.
17. (k) Al-Taweel, S. M. Phosphorus, Sulfur, Silicon 1997, 130, 203.
18. See, Section IV.D.3 in ref 1a.
19. Several planar chiral phosphaferrocenes have been resolved in enantiomerically pure form, see: (a) Ganter, C.; Brassar, L.; Ganter, B. Tetrahedron: Asymmetry 1997, 8, 2607.
20. (b) Ganter, C.; Brassat, L.; Ganter, B. Chem. Ber./Recl. 1997, 130, 1771.
21. (c) Ganter, C.; Brassat, L.; Glinsböckel, C.; Ganter, B. Organometallics 1997, 16, 2862.
22. (d) Ganter, C.; Glinsböckel, C.; Ganter, B. Eur. J. Inorg. Chem. 1998, 1163.
23. (e) Qiao, S.; Hoic, D. A.; Fu, G. C. Organometallics 1998, 17, 773.
24. (f) Qiao, S.; Fu, G. C. J. Org. Chem. 1998, 63, 4168.
25. (g) Ganter, C.; Kaulen, C.; Englert, U. Organometallics 1999, 18, 5444.
26. (h) Shintani, R.; Lo M. M.-C.; Fu, G. C. Org. Lett. 2000, 2, 3695.
27. (i) Tanaka, K.; Qiao, S.; Tobisu, M.; Lo, M. M.-C.; Fu, G. C. J. Am. Chem. Soc. 2000, 122, 9870.
28. (j) Klys, A.; Zakrzewski, J.; Rybarczyk-Pirek, A.; Olszak, T. A. Tetrahedron: Asymmetry 2001, 12, 533.
29. Ogasawara, M.; Yoshida, K.; Hayashi, T. Organometallics 2001, 20, 1014.
30. The eclipse conformation (with respect to the phosphametallocene skeleton) for stable conformers has been proposed by Okuda (refs 4a and 4c) and Orrell (ref 4g).
31. 2M where M = Fe and Ru, have been reported recently and the distances between the two phospholyl ligands in the disphosphametallocenes were 3.34 Å for M = Fe and 3.62 Å for M = Ru (see ref 10).
32. Ogasawara, M.; Nagano, T.; Yoshida, K.; Hayashi, T. Organometallics 2002, 21, 3062.
33. (a) Sandström, J. Dynamic NMR Spectroscopy; Academic Press: London, UK, 1982.
34. (b) The line-shape analyses were performed with the package software gNMR 5, v. 4.1 for Windows (Cherwell Scientific, 1999).
35. 2Ru are 3.32 and 3.68 Å, respectively. See: (a) Dunitz, J. D.; Orgel, L. E.; Rich, A. Acta Crystallogr. 1956, 9, 373.
36. (b) Hardgrove, G. L.; Templeton, D. H. Acta Crystallogr. 1959, 12, 28.
37. ‡ (at 25°C) = 11.8 kcal/mol. However, these values contain a considerable amount of inaccuracy (ca. 10% or more) for the reasons described in the main text, thus we are very reluctant to have a discussion using these values.
38. The restricted rotations of heavily substituted cyclopentadienyl ligands in the bent metallocenes of group IV metals are reported, see refs 4c and 4f.
39. Mathey, F.; de Lauzon, G. Organomet. Synth. 1986, 3, 259.
40. Roberts, R. M. G.; Wells, A. S. Inorg. Chim. Acta 1986, 112, 171.