Hydrolysis of Fischer carbene complexes. Steric effects of the π-donor group

Journal of Organic Chemistry

Volumn 71, Issue 6, 2006, Pages 2395-2401

  Michoff, Martin E Zoloff ^a   De Rossi, Rita H ^a   Granados, Alejandro M ^a  

^a UNIVERSIDAD NACIONAL DE CÓRDOBA   (Argentina)

Author keywords

[No Author keywords available]

Indexed keywords

Π-DONOR GROUP; FISCHER CARBENE COMPLEXES; LINEAR CORRELATIONS; STERIC EFFECTS; STERIC PARAMETERS;

CARBON; CORRELATION METHODS; ESTERS; HYDROLYSIS;

FISCHER-TROPSCH SYNTHESIS;

2 PROPANOL; ACETIC ACID; BENZOIC ACID; CARBENE; FORMIC ACID; PROPANE;

ARTICLE; CHEMICAL REACTION KINETICS; DECOMPOSITION; HYDROLYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

HYDROCARBONS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; METHANE; MOLECULAR STRUCTURE;

EID: 33645016922     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0525377     Document Type: Article

References (57)

1. Dötz, K. H.; Fischer, H.; Hofmann, P.; Kreissl, S. R.; Schubert, U.; Weiss, K. Transition Metal Carbene Complexes; Verlag Chemie: Deerfield Beach, Fl, 1983.
2. Wulff, W. D.; Yang, D. C. J. Am. Chem. Soc. 1984, 106, 7565.
3. Gandler, J. R.; Bernasconi, C. F. Organometallics 1989, 8, 2282.
4. Amyes, T. L.; Richard, J. P. J. Am. Chem. Soc. 1996, 118, 3129.
5. Capriati, V.; Florio, S.; Luisi, R.; Perna, F. M.; Barluenga, J. J. Org. Chem. 2005, 70, 5852.
6. Barluenga, J.; Santamaria, J.; Tomas, M. Chem. Rev. 2004, 104, 2259-2283.
7. Wu, Y. T.; Noltemeyer, M.; de Meijere, A. Eur J. Org. Chem. 2005, 13, 2802-2810.
8. Barluenga, J.; Rodriguez, M.; Fañanas, F. J.; Florez, J. Cycloaddition Reactions of Group 6 Fischer Carbene Complexes in Metal Carbenes in Organic Synthesis; Dotz, K. H., Ed.; Springer-Verlag Berl: Berlin, 2004; pp59-121.
9. Gomez Gallego, M.; Mancheno, M. J.; Sierra, M. A. Acc. Chem. Res. 2005, 38, 44-53.
10. Heckl, B.; Werner, H.; Fischer, E. O. Angew. Chem., Int. Ed. Engl. 1968, 7, 817.
11. Werner, H.; Fischer, E. O. Heckl, B.; Kreiter, C. G. J. Organomet. Chem. 1971, 28, 367.
12. Steinmetz, A. L.; Hershberger, S. A.; Angelice, R. J. Organometallics 1984, 3, 461.
13. Choi, H. S.; Sweigart, D. A. J. Organomet. Chem. 1982, 278, 249.
14. Pickering, R. A.; Angelici, R. J. J. Organomet. Chem. 1982, 225, 253.
15. Bernasconi, C. F.; Flores, F. X.; Gandler, J. TR.; Leyes, A. E. Organometallics 1994, 13, 1186.
16. Bernasconi, C. F.; Garcia-Rio, L. J. Am. Chem. Soc. 2000, 122, 3821.
17. Bernasconi, C. F.; Flores, F. X.; Sun, W. J. Am. Chem. Soc. 1995, 117, 4875.
18. Bernasconi, C. F.; Flores, F. X.; Kittredge, K. W. J. Am. Chem. Soc. 1997, 119, 2103.
19. Bernasconi, C. F.; Leyes, A. E. J. Chem. Soc., Perkin Trans. 2 1997, 1641.
20. Bernasconi, C. F.; Perez, G. S. J. Am. Chem. Soc. 2000, 122, 12461.
21. Bernasconi, C. F.; Bhattacharya, S. Organometallics 2004, 23, 1723.
22. Bernasconi, C. F.; Flores, F. X.; Kittredge, K. W. J. Am. Chem. Soc. 1998, 120, 8575.
23. Bernasconi, C. F.; Kittredge, K. W.; Flores, F. X. J. Am. Chem. Soc. 1999, 121, 6630.
24. Bernasconi, C. F.; Ali, M. J. Am. Chem. Soc. 1999, 121, 11384.
25. Bernasconi, C. F.; Stronach, M. W. J. Am. Chem. Soc. 1993, 115, 11384.
26. Bernasconi, C. F.; Whitesell, C.; Johnson, R. A. Tetrahedron 2000, 56, 4917.
27. Bernasconi, C. F.; Bhattacharya, S. Organometallics 2003, 22, 426.
28. Bernasconi, C. F.; Bhattacharya, S. Organometallics 2003, 22, 1310.
29. Bernasconi, C. F.; Ali, M. Organometallics 2004, 23, 6134.
30. The intrinsic barrier is the barrier in the absence of a thermodynamic driving force.
31. Bernasconi, C. F.; Ali, M. J. Am. Chem. Soc. 1999, 121, 11384.
32. Bernasconi, C. F.; Sun, W. Organometallics 1995, 14, 5615.
33. See the Supporting Information.
34. 2′ 10.6.
35. Jenks, W. P. J. Am. Chem. Soc. 1972, 94, 4731.
36. (a) Bernasconi, C. F.; Flores, F. X.; Gandler, J. R.; Leyes, A. E. Organometallics 1994, 13, 2193.
37. (b) Bernasconi, C. F.; Ali, M. J. Am. Chem. Soc. 1999, 121, 3039.
38. Mansch, C.; Leo, A.: Taft, R. W. Chem. Rev. 1991, 91, 165.
39. Pavelich, W. A.; Taft, R. W. J. Am. Chem. Soc. 1957, 79, 4935.
40. Hancock, C. K.; Meyers, E. A.; Yager, B. J. J. Am. Chem. Soc. 1961, 83, 4211.
41. Idoux, J. P.; Scherck, J.O. J. Org. Chem. 1978, 43, 4002.
42. Charton, M. J. Org. Chem. 1977, 41, 3531.
43. Bernasconi, C. F.; Murray, C. J.; Fox, J. P.; Carre, D. J. J. Am. Chem. Soc. 1983, 105, 4349.
44. Barluenga, J.; Trabanco, A. A.; Flores, J.; Garcia-Granda, S.; Martín, E. J. Am. Chem. Soc. 1996, 118, 13099.
45. Bernasconi, C. F. The Physical Organic Chemistry of Fischer Carbene Complexes. Adv. Phys. Org. Chem. 2002, 37, 137-237.
46. -1.
47. -1.
48. 1.
49. 0.
50. Hammond, G. S. J. Am. Chem. Soc. 1955, 77, 334.
51. Williams, A. Free Energy Relationships; The Royal Society of Chemistry: Cambridge., UK, 2003; p 109.
52. Semmelhack, M. F.; Bozell, J. J. Tetrahedron Lett. 1982m 23, 2931.
53. See also: Fischer, E. O.; Selmayr, T.; Kreissl, F. R. Chem. Ber. 1977, 110, 2947.
54. Soderberg, B. C; Hegedus, L. S.; Sierra, M. A. J. Am. Chem. Soc. 1990, 112, 4364.
55. Barluenga, J.; Monserrat, J. M.; Flórez, J.; Garcia-Granda. S.; Martin, E., Angew. Chem., Int. Ed. 1994, 33, 1392.
56. 1 = (-)-8-phenylmenthyl. See: Dötz, K. H.; Stinner, C.; Nieger, M J. Chem. Soc., Chem. Commun 1995, 2535.
57. Allen, A. D.; Tidwell, T. T. J. Am. Chem. Soc. 1987, 109, 2704.