The noncarbonylative photochemistry of group 6 fischer carbene complexes

European Journal of Inorganic Chemistry

Volumn , Issue 15, 2008, Pages 2454-2462

  Fernández, Israel ^a   Sierra, Miguel A ^a   Mancheño, María José ^a   Gómez Gallego, Mar ^a   Cossío, Fernando P ^b  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b UNIVERSITY OF THE BASQUE COUNTRY UPV EHU   (Spain)

Author keywords

Excited states; Metal carbenes; Photochemistry; Type I dyotropic rearrangements; fragmentation

Indexed keywords

ATOMS; CHROMIUM COMPOUNDS; COMPUTATION THEORY; GROUP THEORY; HYDROGEN; NITROGEN; PHOTOCHEMICAL REACTIONS; POTENTIAL ENERGY; QUANTUM CHEMISTRY; TUNGSTEN COMPOUNDS;

CARBENE COMPLEXES; COMPUTATIONAL STUDIES; DENSITY-FUNCTIONAL-THEORY; EXCITED-STATES; FISCHER CARBENE COMPLEX; METAL CARBENES; NITROGEN ATOM; REACTION MECHANISM; TYPE I DYOTROPIC REARRANGEMENT; Α-FRAGMENTATION;

DENSITY FUNCTIONAL THEORY;

EID: 53049091105     PISSN: 14341948     EISSN: 10990682     Source Type: Journal    
DOI: 10.1002/ejic.200800146     Document Type: Article

References (64)

1. a) L. S. Hegedus, R. Imwinkelried, M. Alarid-Sargent, D. Dvorak, Y. Satoh, J. Am. Chem. Soc. 1990, 112, 1109;
2. b) L. S. Hegedus, J. Montgomery, Y. Narukawa, D. C. Snustad, J. Am. Chem. Soc. 1991, 113, 5784;
3. c) Y. Narukawa, K. N. Juneau, D. C. Snustad, D. B. Miller, L. S. Hegedus, J. Org. Chem. 1992, 57, 5453.
4. a) M. A. Sierra, L. S. Hegedus, J. Am. Chem. Soc. 1989, 111, 2335;
5. b) B. C. Soderberg, L. S. Hegedus, M. A. Sierra, J. Am. Chem. Soc. 1990, 112, 4364;
6. c) L. S. Hegedus, R. W. Bates, B. C. Söderberg, J. Am. Chem. Soc. 1991, 113, 923.
7. a) L. S. Hegedus, M. A. Schwindt, S. DeLombaert, R. Imwinkelried, J. Am. Chem. Soc. 1990, 112, 2264;
8. b) J. R. Miller, S. R. Pulley, L. S. Hegedus, S. DeLombaert, J. Am. Chem. Soc. 1992, 114, 5602.
9. C. A. Merlic, D. Xu, J. Am. Chem. Soc. 1991, 113, 7418.
10. P. J. Colson, L. S. Hegedus, J. Org. Chem. 1994, 59, 4972.
11. Reviews on the photochemistry of group 6 metal carbene complexes: a) M. A. Schwindt, J. R. Miller, L. S. Hegedus, J. Organomet. Chem. 1991, 413, 143;
12. b) L. S. Hegedus in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon, Oxford, 1995, p. 549;
13. c) L. S. Hegedus, Tetrahedron 1997, 53, 4105.
14. Selected reviews on the chemistry and synthetic applications of Fischer carbene complexes: a) K. H. Dötz, H. Fischer, P. Hofmann, R. Kreissl, U. Schubert, K. Weiss, Transition Metal Carbene Complexes, VCH, Deerfield Beach, Florida, 1983;
15. b) K. H. Dötz, Angew. Chem. 1984, 96, 573;
16. Angew. Chem. Int. Ed. Engl. 1984, 23, 587;
17. c) W. D. Wulff in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming), Pergamon, Oxford, 1991, p. 1065;
18. d) W. D. Wulff in Comprehensive Organometallic Chemistry II, Vol. 12 (Eds.: E. W. Abel, F. G. A. Stone, G. Wilkinson), Pergamon: Oxford. 1995, p. 470;
19. e) D. F. Harvey, D. M. Sigano, Chem. Rev. 1996, 96, 271;
20. f) R. Aumann, H. Nienaber, Adv. Organomet. Chem. 1997, 41, 163;
21. g) M. A. Sierra, Chem. Rev. 2000, 100, 3591;
22. h) J. Barluenga, F. J. Fañanás, Tetrahedron 2000, 56, 4597;
23. i) A. de Meijere, H. Schirmer, M. Duetsch, Angew. Chem. 2000, 112, 4142;
24. Angew. Chem. Int. Ed. 2000, 39, 3964;
25. j) J. Barluenga, J. Flórez, F. J. Fañanás, J. Organomet. Chem. 2001, 624, 5;
26. k) J. Barluenga, J. Santamaría, M. Tomás, Chem. Rev. 2004, 104, 2259;
27. l) M. Gómez-Gallego, M. J. Mancheño, M. A. Sierra, Acc. Chem. Res. 2005, 38, 44;
28. m) M. A. Sierra, M. Gómez-Gallego, R. Martínez- Álvarez, Chem. Eur. J. 2007, 13, 736.
29. a) I. Fernández, M. A. Sierra, M. Gómez-Gallego, M. J. Mancheño, F. P. Cossío, Chem. Eur. J. 2005, 11, 5988;
30. b) A. Arrieta, F. P. Cossío, I. Fernández, M. Gómez-Gallego, B. Lecea, M. J. Mancheño, M. A. Sierra, J. Am. Chem. Soc. 2000, 122, 11509.
31. The irradiation of chromium(0)- and tungsten(0)-carbene complexes with UV light promoted the loss of one CO ligand. However, up until today no useful chemistry based on this fact has been reported. See: a) H. C. Foley, L. M. Strubinger, T. S. Targos, G. L. Geoffroy, J. Am. Chem. Soc. 1983, 105, 3064;
32. b) P. C. Servaas, D. J. Stufkens, A. Oskam, J. Organomet. Chem. 1990, 390, 61.
33. a) L. S. Hegedus, Tetrahedron 1997, 53, 4105;
34. b) L. S. Hegedus, G. deWeck, S. DAndrea, J. Am. Chem. Soc. 1988, 110, 2122.
35. M. L. Gallager, J. B. Greene, A. D. Rooney, Organometallics 1997, 16, 5260, and the references therein that relate to the earlier attempts to trap the photogenerated ketenes from irradiation of chromium(0)-carbenes.
36. M. A. Sierra, I. Fernández, M. J. Mancheño, M. Gómez-Gallego, M. R. Torres, F. P. Cossío, A. Arrieta, B. Lecea, A. Poveda, J. Jiménez-Barbero, J. Am. Chem. Soc. 2003, 125, 9572.
37. I. Fernández, M. A. Sierra, M. Gómez-Gallego, M. J. Mancheño, F. P. Cossío, Angew. Chem. 2006, 118, 131;
38. Angew. Chem. Int. Ed. 2006, 45, 125.
39. 2Ph in compound 8d.
40. 4). These data indicate that oxidation of the phosphane moiety occurs in compound 9b. Additional ESI-MS confirms the presence of the phosphane oxide moiety in compound 9b (m/z = 359).
41. a) J. D. Coyle, Chem. Rev. 1978, 78, 97;
42. b) A. G. Gilbert, J. Baggott, Essentials of Molecular Photochemistry, Blackwell Science, Oxford, 1991, pp. 328-329.
43. This fragmentation in the position α to the carbene nitrogen atom is predictable on the basis of the isolobal analogy. In fact, complexes 3 and 7 are pentacarbonyl metal complexes analogous to the corresponding amides. See: a) R. Hoffmann, Science 1981, 211, 995;
44. b) R. Hoffmann, Angew. Chem. 1982, 94, 711;
45. Angew. Chem. Int. Ed. Engl. 1982, 21, 711.
46. a) M. T. Reetz, Angew. Chem. 1972, 84, 161;
47. Angew. Chem. Int. Ed. Engl. 1972, 11, 129;
48. b) M. T. Reetz, Tetrahedron 1973, 29, 2189.
49. Stepwise 1,2-dyotropic rearrangements are scarce. To the best of our knowledge, the only other example was reported a few years ago; see: X. Zhang, K. N. Houk, S. Lin, S. Danishefsky, J. Am. Chem. Soc. 2003, 125, 5111.
50. a) C. K. Murray, B. P. Warner, V. Dragisich, W. D. Wulff, R. D. Rogers, Organometallics 1990, 9, 3142;
51. b) I. Fernández, M. J. Mancheño, M. Gómez-Gallego, M. A. Sierra, T. Lejon, L. K. Hansen, Organometallics 2004, 23, 1851.
52. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision C.02, Gaussian, Inc., Wallingford CT, 2004.
53. a) A. D. Becke, J. Chem. Phys. 1993, 98, 5648;
54. b) C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1998, 37, 785;
55. c) S. H. Vosko, L. Wilk, M. Nusair, Can. J. Phys. 1980, 58, 1200.
56. W. J. Hehre, L. Radom, P. v. R. Schleyer, J. A. Pople, Ab initio Molecular Orbital Theory, Wiley, New York, 1986, p. 76 and references cited therein.
57. P. J. Hay, W. R. Wadt, J. Chem. Phys. 1985, 82, 299.
58. These computations were performed at the CIS level of theory starting from the HF wavefunction. See: J. B. Foresman, M. Hedd-Gordon, J. A. Pople, M. J. Frisch, J. Phys. Chem. 1992, 96, 135.
59. J. W. McIver, A. K. Komornicki, J. Am. Chem. Soc. 1972, 94, 2625.
60. C. González, H. B. Schlegel, J. Phys. Chem. 1990, 94, 5523.
61. a) J. P. Foster, F. Weinhold, J. Am. Chem. Soc. 1980, 102, 7211;
62. b) A. E. Reed, F. Weinhold, J. Chem. Phys. 1985, 83, 1736;
63. c) A. E. Reed, R. B. Weinstock, F. Weinhold, J. Chem. Phys. 1985, 83, 735;
64. d) A. E. Reed, L. A. Curtiss, F. Weinhold, Chem. Rev. 1988, 88, 899.