Conformation-Reactivity Relationships for the Organotransition-Metal Complexes (η5-C5H5)Fe(CO)(PPh3)R and (η5-C5H5)Re(NO)(PPh3)R (R = Alkyl and Aryl)

Journal of the American Chemical Society

Volumn 107, Issue 23, 1985, Pages 6522-6531

  Seeman, Jeffrey I ^a   Davies, Stephen G ^b  

^a Philip Morris USA Research Center   (United States)

^b UNIVERSITY OF OXFORD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001428497     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00309a018     Document Type: Article

References (66)

1. Davies, S. G. “Organotransition Metal Chemistry: Application to Organic Synthesis”; Pergamon Press: Oxford, 1982.
2. Collman, J. P.; Hegedus, L. S. “Principles and Applications of Organotransition Metal Chemistry”; University Science Books: Mill Valley, CA, 1980.
3. Wilkinson G.; Stone, F. G. A.; Abel, E. W. “Comprehensive Organometallic Chemistry”; Pergamon Press: Oxford, 1982.
4. For a set of rules which allow the prediction of nucleophilic attack regiochemistry on 18-electron organotransition-metal cations containing unsaturated ligands, see: Davies, S. G.; Green, M. L. H.; Mingos, D. M. P. Tetrahedron 1978, 34, 3047; Tetrahedron Rep. 1978, No. 57, 1.
5. Colquhoun, H. M.; Holton, J.; Thompson, D. J.; Twigg, M. V. “New Pathways for Organic Synthesis”; Plenum Press: New York, 1984.
6. Davies, S. G.; Dordor, I. M.; Walker, J. C.; Warner, P. Tetrahedron Lett. 1984, 2709.
7. Davies, S. G.; Seeman, J. I. Tetrahedron Lett. 1984, 1845.
8. Davies, S. G.; Dordor, I. M.; Warner, P. J. Chem. Soc., Chem. Commun. 1984, 956.
9. Baird, G. J.; Davies, S. G.; Jones, R. H.; Prout, K.; Warner, P. J. Chem. Soc., Chem. Commun. 1984, 745.
10. Curtis, P. J.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1984, 747.
11. Baird, G. J.; Bandy, J. A.; Davies, S. G.; Prout, K. J. Chem. Soc., Chem. Commun. 1983, 1202.
12. Baird, G. J.; Davies S. G.; Maberly, T. R. Organometallics 1984, 3, 1764.
13. (a) Liebeskind, L. S.; Welker, M. E.; Goedken, V. J. Am. Chem. Soc. 1984, 106, 441. (b) Liebeskind, L. S.; Welker, M. E. Tetrahedron Lett. 1984, 4341.
14. Brunner, H.; Hammer, B.; Bernal, I.; Draux, M. Organometallics 1983, 2, 1595.
15. Brunner, H. Adv. Organomet. Chem. 1980, 18, 151.
16. Flood, T. C.; Campbell, K. D. J. Am. Chem. Soc. 1984, 106, 2853.
17. Jensen, J. E.; Campbell, L. L.; Nakanishi, S.; Flood, T. C. J. Organomet. Chem. 1983, 244, 61.
18. Flood, T. C. Top. Stereochem. 1981, 12, 37.
19. Brookhart, M.; Timmers, D.; Tucker, J. R.; Williams, G. D.; Husk, G. R.; Brunner, H.; Hammer, B. J. Am. Chem. Soc. 1983, 105, 6721.
20. Brookhart, M.; Tucker, J. R.; Husk, G. R. J. Am. Chem. Soc. 1983, 105, 258.
21. Bodnar, T.; Cutler, A. R. J. Organomet. Chem. 1981, 213, C31-C36.
22. Davison, A.; Reger, D. L. J. Am. Chem. Soc. 1972, 94, 9237.
23. Reger, D. L.; Belmore, K. A.; Mintz, E.; McElligott, P. J. Organometallics 1984, 3, 134.
24. Reger, D. L.; Belmore, K. A.; Atwood, J. L.; Hunter, W. E. J. Am. Chem. Soc. 1983, 105, 5710.
25. Reger, D. L.; McElligott, P. J.; Charles, N. G.; Griffith, E. A. H.; Amma, E. L. Ogranometallics 1982, 1, 443.
26. Kiel, W. A.; Buhro, W. E.; Gladysz, J. A. Organometallics 1984, 3, 879.
27. Buhro, W. E.; Wong, A.; Merrifield, J. H.; Lin, G.-Y.; Constable, A. C.; Gladysz, J. A. Organometallics 1983, 2, 1852.
28. Hatton, W. G.; Gladysz, J. A. J. Am. Chem. Soc. 1983, 105, 6157.
29. Patton, A. T.; Strouse, C. E.; Knobler, C. B.; Gladysz, J. A. J. Am. Chem. Soc. 1983, 105, 5804.
30. Merrifield, J. H.; Lin, G.-Y.; Kiel, W. A.; Gladysz, J. A. J. Am. Chem. Soc. 1983, 105, 5811.
31. Kiel, W. A.; Lin, G.-Y.; Bodner, G. S.; Gladysz, J. A. J. Am. Chem. Soc. 1983, 105, 4958.
32. Kiel, W. A.; Lin, G.-Y.; Constable, A. G.; McCormick, F. B.; Strouse, C. E.; Eisenstein, O.; Gladysz, J. A. J. Am. Chem. Soc. 1982, 104, 4865.
33. Tam, W.; Lin, G.-Y.; Wong, W.-K.; Kiel, W. A.; Wong, V. K.; Gladysz, J. A. J. Am. Chem. Soc. 1982, 104, 141.
34. See, for example: Theopold, K. H.; Becker, P. N.; Bergman, R. G. J. Am. Chem. Soc. 1982, 104, 5250.
35. For a preliminary report of some of these results, see: Seeman, J. I.; Davies, S. G. J. Chem. Soc., Chem. Commun. 1984, 1019.
36. This model appears frequently in the very recent edition of the Gmelin Handbook in the iron series: “Gmelin Handbook of Inorganic Chemistry”; Springer-Verlag: Berlin, 1983: Vol. B11.
37. Thomson, J.; Keeney, W.; Baird, M. C.; Reynolds, W. F. J. Organomet. Chem. 1972, 40, 205.
38. Stanley, K.; Zelonka, R. A.; Thomson, J.; Fiess, P.; Baird, M. C. Can. J. Chem. 1974, 52, 1781.
39. Stanley, K.; Baird, M. C. Inorg. Nucl. Chem. Lett. 1974, 10, 1111.
40. Stanley, K.; Baird, M. C. J. Am. Chem. Soc. 1975, 97, 6598.
41. Stanley, K.; Baird, M. C. J. Am. Chem. Soc. 1975, 97, 4292.
42. Stanley, K.; Baird, M. C. J. Am. Chem. Soc. 1977, 99, 1808.
43. For an examination and exploration of organotransition-metal complex structure and chemistry through the use of the extended Hiickel procedure, see the numerous reports of the Hoffmann school at Cornell University, Ithaca, NY. For the early papers on this method, see: Hoffmann, R. J. Chem. Phys. 1963, 39, 1397. Hoffmann, R.; Lipscomb, W. N. J. Chem. Phys. 1962, 36, 2179, 3489; 1962, 37, 2872.
44. Merrifield, J. H.; Strouse, C. E.; Gladysz, J. A. Organometallics 1982, 1, 1204.
45. Flood, T. C.; Rosenberg, E.; Sarhangi, A. J. Am. Chem. Soc. 1977, 99, 4334.
46. Chou, C.-K.; Miles, D. L.; Bau, R.; Flood, T. C. J. Am. Chem. Soc. 1978, 100, 7271.
47. Semion, V. A.; Struchkov, Yu. T. J. Struct. Chem. (Engl. Transl.) 1969, 10, 80.
48. Einstein, F. W. B.; Restivo, R. Inorg. Chim. Acta 1971, 5, 501.
49. Semion, V. A.; Struchkov, Yu. T. J. Struct. Chem. (Engl. Transl.) 1969, 10, 563.
50. Attig, T. G.: Teller. R. G.; Wu, S.-M.; Bau, R.: Wojcicki, A. J. Am. Chem. Soc. 1979, 101, 619.
51. Miles, S. L.; Miles, D. L.; Bau, R.; Flood, T. C. J. Am. Chem. Soc. 1978, 100, 7278.
52. Reisner, M. G.; Bernal, I.; Brunner, H.; Muschiol, M. Inorg. Chem. 1978, 17, 783.
53. Andrianov, V. G.; Sergeeva, G. N.; Struchkov, Yu. T.; Anisimov, K. N.; Kolobova, N. E.; Beshastnov, A. S. J. Struct. Chem. (Engl. Transl.) 1970, 11, 163.
54. Buhro, W. E.; Patton, A. T.; Strouse, C. E.; Gladysz, J. A.; McCormick, F. B.; Etter, M. C. J. Am. Chem. Soc. 1983, 105, 1056.
55. Wong, W.-K.; Tam, W.; Strouse, C. E.; Gladysz, J. A. J. Chem. Soc., Chem. Commun. 1979, 530.
56. Hofmann, P. Angew. Chem., Int. Ed. Engl. 1977, 16, 536.
57. Schilling, B. E. R.; Hoffmann, R.; Lichtenberger, D. L. J. Am. Chem. Soc. 1979, 101, 585.
58. Berke, H.; Hoffmann, R. J. Am. Chem. Soc. 1978, 100, 7224.
59. Goddard, R. J.; Hoffmann, R.; Jemmis, E. D. J. Am. Chem. Soc. 1980, 102, 7667.
60. Ortiz, J. V.; Havlas, Z.; Hoffmann, R. Helv. Chim. Acta 1984, 67, 1.
61. Kubáček, P.; Hoffmann, R.; Havlas, Z. Organometallics 1982, 1, 180.
62. Seeman, J. I. Chem. Rev. 1983, 83, 83.
63. Cutler, A. R. J. Am. Chem. Soc. 1979, 101, 604.
64. 3)CHMeOMe, see: Bodnar, T.; Cutler, A. R. J. Organomet. Chem. 1981, 213, C31-C36.
65. Hunter, B. K.; Baird, M. C. unpublished results. We thank Prof. Baird for making these results available to us prior to publication.
66. Cameron, A. D.; Baird, M. C. J. Chem. Soc., Dalton Trans., in press.