Photochemistry of imine-group VI carbene complexes with alkenes: Synthetic scope and photochemical aspects

Organometallics

Volumn 21, Issue 20, 2002, Pages 4076-4083

  Campos, Pedro J ^a   Sampedro, Diego ^a   Rodríguez, Miguel A ^a  

^a UNIVERSITY OF LA RIOJA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANATION;

MOLECULAR STRUCTURE; OLEFINS; PHOTOCHEMICAL REACTIONS; QUANTUM THEORY; QUENCHING;

COMPLEXATION;

EID: 0038109960     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0202625     Document Type: Article

References (38)

1. Reviews: (a) Hegedus, L. S. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, p 549.
2. (b) Hegedus, L. S. Tetrahedron. 1997, 53, 4105.
3. Hegedus, L. S.; Schultze, L. M.; Montgomery, J. Organometallics 1989, 8, 2189.
4. Campos, P. J.; Sampedro, D.; Rodríguez, M. A. Organometallics 2000, 19, 3082.
5. Campos, P. J.; Sampedro, D.; Rodríguez, M. A. Tetrahedron Lett. 2002, 43, 73.
6. Montforts, F.-P.; Gerlach, B.; Höper, F. Chem. Rev. 1994, 94, 327 and references therein.
7. Tehrani, K. A.; Borremans, D.; De Kimpe, N. Tetrahedron 1999, 55, 4133 and references therein.
8. (a) Gagosz, P.; Zard, S. Z. Synlett 1999, 1978.
9. (b) Duncan, D.; Livin-ghouse, T. Organometallics 1999, 18, 4421.
10. (c) Bolvin, J.; Schiano, A.-M.; Zard, S. Z.; Zhang, H. Tetrahedron Lett. 1999, 40, 4531.
11. Kanauss, L.; Fischer, E.O. Chem. Ber. 1970, 103, 3744.
12. -1) due to the CO ligands.
13. Aumann, R.; Althaus, S.; Krüger, C.; Betz, P. Chem. Ber. 1989, 122, 357.
14. Murray, C. K.; Warner, B. P.; Dragisich, V.; Wulff, W. D. Organometallics 1990, 9, 3142.
15. See, for example: Jackman, L. M.; Sternhell, S. Applications of Nuclear Magnetic Resonance Spectroscopy in Organic Chemistry; Pergamon Press: Oxford, U.K., 1972; p 94.
16. Steric demand may be classified by the conformational free-energy values for substituted cyclohexanes (-ΔG° (kcal/mol): Ph, 3.1; Et, 1.75). See, for example: Isaacs, N. S. Physical Organic Chemistry; Longman: Harlow, U.K., 1987; p 312.
17. Cycloaddition reactions of Fischer carbene complexes and alkenes usually proceed stereospecifically to give the isomer with a relative trans relationship between the more bulky groups. See for example: Barluenga, J.; Tomqás, M.; López-Pelegrfn, J.; Rubio, E. J. Chem. Soc., Chem. Commun. 1995, 655.
18. Review: Hudlicky, T.; Reed, J. W. In Comprehensive Organic Chemistry; Trost, B. M., Fleming, I., E.; Pergamon: Oxford, U.K., 1991; Vol. 5, p 899.
19. For a preliminary communication see: Campos, P. J.; Soldevilla, A.; Sampedro, D.; Rodríguez, M. A. Org. Lett. 2001, 3, 4087.
20. 2O, 4.4 g/L; NH3, 2.7 M. See for example: CRC Handbook of Organic Photochemistry; Scaiano, J. C., Ed.; CRC Press: Boca Raton, FL, 1989; Vol. I, p 48.
21. 2] in hexane (20 °C) 0.015 M: Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd ed.; Marcel Dekker: New York, 1993; p 289.
22. Lees, A. J. Chem. Rev. 1987, 87, 711.
23. 2 as quencher is complicated by the fact that carbene complexes undergo a facile photooxidation.
24. See ref 18, p 54.
25. See ref 18, p 183.
26. Turro N. J. Modern Molecular Photochemistry; University Science Books: Sausalito, CA, 1991; p 253.
27. See ref 18, p 309.
28. See ref 18, p 314.
29. 3 at 110 °C for 12 h. On the other hand, the irradiation of 1 and methyl vinyl ketone under a CO atmosphere for 1 h only inhibits the formation of 6 in a 5% amount.
30. After irradiation of Fischer carbene complexes, similar coordinated structures has been isolated for intramolecular processes: (a) Barluenga, J.; Aznar, P.; Gutiérrez, I.; Martin, A.; García-Granda, S.; Llorca-Baragaño, M. A. J. Am. Chem. Soc. 2000, 122, 1314.
31. (b) Toledano, C. A.; Rudler, H.; Daran, J.-C.; Jeannin, Y. J. Chem. Soc., Chem. Commun. 1984, 574.
32. (a) Barluenga, J.; López, S.; Trabanco, A. A.; Fernández-Acebes, A.; Flórez, J. J. Am. Chem. Soc. 2000, 122, 8145.
33. (b) Buchert, M.; Reissig, H.-U. Chem. Bar. 1992, 128, 2723.
34. (c) Harvey, D. F.; Lund, K. P. J. Am. Chem. Soc. 1991, 113, 8916.
35. To carry out cyclopropanation processes with electron-rich olefins, it is necessary to use high CO pressures to avoid metathesis. See for example: (a) Fischer, E. O.; Dö'tz, K. H. Chem. Ber. 1972, 105, 3966.
36. (b) Dorrer, B.; Fischer, E. O.; Kalbfus, W. J. Organomet. Chem. 1974, 81, C20.
37. Wulff, W. D.; Yang, D. C.; Murray, C. K. Pure Appl. Chem. 1988, 60, 137.
38. Propiophenone and 2-pentanone imines were prepared according to: Barluenga, J.; Joglar, J.; Fustero, S.; Gotor, V.; Krüger, C.; Romao, M. J. Chem. Ber. 1985, 118, 3652.