Photoreactions of γ,δ-unsaturated chromium carbene complexes

Journal of the American Chemical Society

Volumn 118, Issue 34, 1996, Pages 7873-7880

  Moser, William H ^a   Hegedus, Louis S ^a  

^a Department of Environmental and Radiological Health Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMIUM DERIVATIVE; METAL COMPLEX;

ARTICLE; PHOTOCHEMISTRY; STEREOCHEMISTRY;

EID: 0029789262     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9537585     Document Type: Article

References (41)

1. For reviews see: (a) Dötz, K. H. Angew. Chem. Int. Ed. Engl. 1984, 23, 587. (b) Wulff, W. D. Metal Carbene Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: London, 1991; Vol. 5, pp 1065-1113.
2. For reviews see: (a) Dötz, K. H. Angew. Chem. Int. Ed. Engl. 1984, 23, 587. (b) Wulff, W. D. Metal Carbene Cycloadditions. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: London, 1991; Vol. 5, pp 1065-1113.
3. Dötz, K. H. Angew. Chem., Int. Ed. Engl 1975, 14, 644.
4. Dötz, K. H. New J. Chem. 1990, 14, 433. For a recent, comprehensive review see: Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, UK, 1995; Vol. 12, pp 469-547.
5. Dötz, K. H. New J. Chem. 1990, 14, 433. For a recent, comprehensive review see: Wulff, W. D. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, UK, 1995; Vol. 12, pp 469-547.
6. (a) Merlic, C. A.; Xu, D. J. Am. Chem Soc. 1991, 113, 7418.
7. (b) Merlic, C. A.; Xu, D. J. Org. Chem. 1993, 58, 538.
8. (a) Freeman, P. K.; Kuper, D. G. Chem. Ind. 1965, 424.
9. (b) Meinwald, J.; Wahl, G. H., Jr. Chem. Ind. 1965, 425.
10. Cannone, P.; Akssira, M. Tetrahedron 1985, 41, 3695.
11. Semmelhack, M. F.; Lee, G. R. Organometallics 1987, 6, 1839.
12. Schwindt, M. A.; Lejon, T.; Hegedus, L. S. Organometallics 1990, 9, 2814.
13. Valenti, E.; Pericàs, M. A.; Moyano, A. J. Org. Chem. 1990, 55, 3582.
14. Wiberg, K. B.; Lowry, B. R.; Nist, B. J. J. Am. Chem. Soc. 1962, 84, 1594.
15. For reviews see: (a) Snider, B. B. Chem. Rev. 1988, 88, 793. (b) Ernst, B.; DeMesmaeker, A.; Hans, G.; Veenstra, S. J. NATO ASI Ser., Ser. C 1989, 273, 207. (c) Hyatt, J. A.; Raynolds, P. W. Org. React. 1994, 45, 159.
16. For reviews see: (a) Snider, B. B. Chem. Rev. 1988, 88, 793. (b) Ernst, B.; DeMesmaeker, A.; Hans, G.; Veenstra, S. J. NATO ASI Ser., Ser. C 1989, 273, 207. (c) Hyatt, J. A.; Raynolds, P. W. Org. React. 1994, 45, 159.
17. For reviews see: (a) Snider, B. B. Chem. Rev. 1988, 88, 793. (b) Ernst, B.; DeMesmaeker, A.; Hans, G.; Veenstra, S. J. NATO ASI Ser., Ser. C 1989, 273, 207. (c) Hyatt, J. A.; Raynolds, P. W. Org. React. 1994, 45, 159.
18. (a) Snider, B. B.; Hui, R. A. H. F. J. Org. Chem. 1985, 50, 5167.
19. (b) Soderberg, B. C.; Hegedus, L. S.; Sierra, M. A. J. Am. Chem. Soc. 1990, 112, 4364.
20. Lutz, R. P. Chem. Rev. 1984, 84, 205.
21. Calculations were carried out on a Silicon Graphics Iris computer using Micromodel Version 4.0. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8124. Liljefor, T.; Tai, J. C.; Li, S.; Allinger, N. L. J. Comp. Chem. 1987, 8, 1051. Sprague, J. T.; Tai, J. C.; Yuh, Y.; Allinger, N. L. J. Comp. Chem. 1987, 8, 581.
22. Calculations were carried out on a Silicon Graphics Iris computer using Micromodel Version 4.0. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8124. Liljefor, T.; Tai, J. C.; Li, S.; Allinger, N. L. J. Comp. Chem. 1987, 8, 1051. Sprague, J. T.; Tai, J. C.; Yuh, Y.; Allinger, N. L. J. Comp. Chem. 1987, 8, 581.
23. Calculations were carried out on a Silicon Graphics Iris computer using Micromodel Version 4.0. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8124. Liljefor, T.; Tai, J. C.; Li, S.; Allinger, N. L. J. Comp. Chem. 1987, 8, 1051. Sprague, J. T.; Tai, J. C.; Yuh, Y.; Allinger, N. L. J. Comp. Chem. 1987, 8, 581.
24. NMR measurments were carried out and interpreted by Dr. Chris Rithner of this department. We thank an astute referee for suggesting structure 8 as a more reasonable structure than the 2-decalinone regioisomer originally proposed by the authors, and for suggesting an alternate mechanism for its formation.
25. Chromium-mediated [2 + 2] cycloaddition in both ketene - olefin and ketene - imine reactions has been previously proposed to rationalize differences in stereochemistry between these reactions involving free ketenes and those involving photogenerated chromium-ketene complexes. Hegedus, L. S.; Montgomery, J.; Narukawa, Y.; Snustad, D. C. J. Am. Chem. Soc. 1991, 113, 5784.
26. Slack, D. A.; Egglestone, D. L.; Baird, M. C. J. Organomet. Chem. 1978, 146, 71.
27. Hafner, A.; Hegedus, L. S.; deWeck, G.; Hawkins, B.; Dötz, K. H. J. Am. Chem. Soc. 1988, 110, 8413.
28. This procedure results in some dialkylation: Casey, C. P.; Brunsvold, W. R. J. Organomet. Chem. 1976, 118, 309. In our hands, typically <10% of the dialkylated product was observed, which was not problematic when carried on to subsequent steps.
29. Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy; John Wiley and Sons, Ltd.: New York, 1988; p 497.
30. See, for examples: Ziegler, F. E.; Petersen, A. K. J. Org. Chem. 1994, 59, 2707.
31. See: Ihara, M.; Taniguchi, T.; Tokunaga, Y.; Fukumoto, K. J. Org. Chem. 1994, 59. 8092 and references therein.
32. Brown, J. M.; Golding, B. T.; Stofko, J. J., Jr. J. Chem. Soc:, Chem. Commun. 1973, 319.
33. Dauben, W. G.; Dinges, J.; Smith, T. C. J. Org. Chem. 1993, 58, 7635.
34. Hudlicky, T.; Kutchan, T. M.; Naqui, S. M. Org. React. 1984, 33, 247.
35. Based on arguments in: (a) Zimmerman, H. E. In Pericyclic Reactions; Marchand, A. P., Lehr, R. E., Eds.; Academic Press: New York, 1977; Vol. I, p 77. (b) Ghosez, L.; O'Donnell, M. J. In Pericyclic Reactions; Marchand, A. P., Lehr, R. E., Eds.; Academic Press: New York, 1977; Vol. H, p 87.
36. Based on arguments in: (a) Zimmerman, H. E. In Pericyclic Reactions; Marchand, A. P., Lehr, R. E., Eds.; Academic Press: New York, 1977; Vol. I, p 77. (b) Ghosez, L.; O'Donnell, M. J. In Pericyclic Reactions; Marchand, A. P., Lehr, R. E., Eds.; Academic Press: New York, 1977; Vol. H, p 87.
37. Hegedus, L. S.; Schwindt, M. A.; De Lombaert, S.; Imwinkelried, R. J. Am. Chem. Soc. 1990, 112, 2264.
38. Herndon, J. W.; McMullen, L. A, J. Am. Chem. Soc. 1989, 111, 6854.
39. Gupta, D.; Somar. R.; Dev, S. Tetrahedron 1982, 38, 3013.
40. Ortiz de Montellano, P. R.; Dinzio, S. E. J Org. Chem. 1978, 43, 4323.
41. Prepared according to literature procedure: Fischer, E.O.; Maasböl, A. Chem. Ber. 1967, 100, 2445.