Oxapentadienyl-rhodium-phosphine chemistry

Organometallics

Volumn 21, Issue 20, 2002, Pages 4099-4112

  Bleeke, John R ^a   Donnay, Edward ^a   Rath, Nigam P ^b  

^a WASHINGTON UNIVERSITY   (United States)

^b UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; COMPLEXATION; ISOMERIZATION; ISOMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY DIFFRACTION ANALYSIS;

NUCLEOPHILES;

ORGANOMETALLICS;

EID: 0037772424     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om020429u     Document Type: Article

References (52)

1. Pentadienyl-Metal-Phosphine Chemistry. 31. Part 30: Bleeke, J. R.; Ortwerth, M. F.; Rohde, A. M. Organometallics 1995, 14, 2813.
2. For reviews, see: (a) Ernst, R. D. Chem. Rev. 1988, 88, 1255.
3. (b) Yasuda, H.; Nakamura, A. J. Organomet. Chem. 1985, 285, 15.
4. (c) Powell, P. Adv. Organomet. Chem. 1986, 26, 125.
5. (d) Ernst, R. D. Comments Inorg. Chem. 1982, 21, 285.
6. For examples of (oxapentadienyl)metal complexes, see: (a) Parshall, G. W.; Wilkinson, G. Inorg. Chem. 1962, 1, 896.
7. (b) Tsuji, J.; Imamura, S.; Kiji, J. Am. Chem. Soc. 1964, 86, 4491.
8. (c) Bannister, W. D.; Green, M.; Haszeldine, R. N. J. Chem. Soc. A 1966, 194.
9. (d) Green, M.; Hancock, R. I. J. Chem. Soc. A 1968, 109.
10. (e) Bennett, R. L.; Bruce, M. I. Aust. J. Chem. 1975, 28, 1141.
11. (f) White, C.; Thompson, S. J.; Maitlis, P. M. J. Organomet. Chem. 1977, 134, 319.
12. (g) Baudry, D.; Daran, J.-C.; Dromzee, Y.; Ephritikhine, M.; Felkin, H.; Jeannin, Y.; Zakrzewski, J. J. Chem. Soc., Chem. Commun. 1988, 813.
13. (h) Benyunes, S. A.; Green, M.; Grimshire, M. J. Organometallics 1989, 8, 2268.
14. (i) Cheng, M.-H.; Wu, Y.-J.; Wang, S.-L.; Liu, R.-S. J. Organomet. Chem. 1989, 373, 119.
15. (j) Cheng, M.-H.; Cheng, C.-Y.; Weng, S.-L.; Peng, S.-M.; Liu, R.-S. Organometallics 1990, 9, 1853.
16. (k) Masters, A. P.; Richardson, J. F.; Sorensen, T. Can. J. Chem. 1990, 88, 2221.
17. (l) Benyunes, S. A.; Day, J. P.; Green, M.; Al-Saadoon, A. W.; Waring, T. L. Angew. Chem., Int. Ed. Engl. 1990, 29, 1416.
18. (m) Benyunes, S. A.; Binelli, A.; Green, M.; Grimshire, M. J. J. Chem. Soc., Dalton Trans. 1991, 895.
19. (n) Vong, W.-J.; Peng, S.-M.; Lin, S.-H.; Lin, W.-J.; Liu, R.-S. J. Am. Chem. Soc. 1991, 113, 573.
20. (o) Schmidt, T.; Goddard, R. J. Chem. Soc., Chem. Commun. 1991, 1427.
21. (p) Trakarnpruk, W.; Arif, A. M.; Ernst, R. D. Organometallics 1992, 11, 1686.
22. (q) Ogoshi, S.; Hirako, K.; Nakanishi, J.; Ohe, K.; Murai, S. J. Organomet. Chem. 1993, 445, C13.
23. (r) AbuBaker, A.; Bryan, C. D.; Cordes, A. W.; Allison, N. T. Organometallics 1994, 13, 3375.
24. (s) Pearson, A. J.; Neagu, I. B.; Pinkerton, A. A.; Kirschbaum, K.; Hardie, M. J. Organometallics 1997, 16, 4346.
25. (t) Söderberg, B. C.; Berry, A.; Jones, P. C. Organometallics 1998, 17, 1069.
26. (u) Beddows, C. J.; Box, M. R.; Butters, C.; Carr, N.; Green, M.; Kursawe, M.; Mahon, M. F. J. Organomet. Chem. 1998, 550, 267.
27. (v) Navarro, M. E.; Chazaro, L. F.; Gonzalez, F. J.; Paz-Sandoval, M. A. J. Electroanal. Chem. 2000, 480, 18.
28. (w) Clemente, M. E. N.; Saavedra, P. J.; Vasquez, M. C.; Paz-Sandoval, M. A.; Arif, A. M.; Ernst, R. D. Organometallics 2002, 21, 592.
29. (a) Bleeke, J. R.; Haile, T.; Chiang, M. Y. Organometallics 1991, 10, 19.
30. (b) Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517.
31. (a) Bleeke, J. R.; Ortwerth, M. F.; Chiang, M. Y. Organometallics 1992, 11, 2740.
32. (b) Bleeke, J. R.; Ortwerth, M. F.; Rohde, A. M. Organometallics 1995, 14, 2813.
33. (a) Bleeke, J. R.; Rohde, A. M.; Robinson, K. Organometallics 1994, 13, 401.
34. (b) Bleeke, J. R.; Rohde, A. M.; Robinson, K. D. Organometallics 1995, 14, 1674.
35. Bleeke, J. R.; Luaders, S. T.; Robinson, K. D. Organometallics 1994, 13, 1592.
36. Van der Ent, A.; Onderdelinden, O. Inorg. Synth. 1973, 14, 92.
37. Heiszwolf, G. J.; Kloosterziel, H. Recl. Trav. Chim. Pays-Bas 1967, 86, 807.
38. Bleeke, J. R.; Haile, T.; New, P. R.; Chiang, M. Y. Organometallics 1993, 12, 517.
39. 3-allyl analogues of 1 and 5 have been reported: Sivak, A. J.; Muetterties, E. L. J. Am. Chem. Soc. 1979, 101, 4878.
40. 1-oxapentadienyl-rhodium intermediate in which C2-C3 bond rotation is facile.
41. 3-2,4-Dimethylpentadienyl analogues of 3 and 4 have been reported: Bleeke, J. R.; Donaldson, A. J. Organometallics 1986, 5, 2401.
42. 31P signals for the minor rotamer overlap coincidentally and hence appear as a single rhodium-coupled doublet.
43. 3 with potassium oxapentadienide: see the Experimental Section.
44. 3 (on the NMR time scale).
45. A somewhat lower temperature is required to broaden the signals due to 2s as compared to those due to 2a.
46. 3 is added to 3 to ensure complete conversion to 7: see Experimental Section.
47. 3's at room temperature.
48. Phosphine dissociation is also indicated by the instability of 7 under vacuum, which has prevented its isolation.
49. 2,4-Dimethylpentadienyl analogues of 8 and 11 have been reported: Bleeke, J. R.; Donaldson, A. J. Organometallics 1988, 7, 1588.
50. - products are formed, along with displaced 2,4-dimethyloxapentadiene. See ref 21 for a similar result in the analogous 2,4-dimethylpentadienyl system.
51. 1-oxapentadienyl complex.
52. Sheldrick, G. M. SHELXTL-PLUS; Bruker Analytical X-ray Division, Madison, WI, 1997.