Preparation of a Resin-Based Chromium Catalyst for Effecting [6π + 2π] Cycloaddition Reactions

Organic Letters

Volumn 2, Issue 24, 2000, Pages 3917-3919

  Rigby, James H ^a   Kondratenko, Mikhail A ^a   Fiedler, Christian ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMIUM; POLYSTYRENE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION;

CATALYSIS; CHROMIUM; CYCLIZATION; POLYSTYRENES;

EID: 0034736315     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0002931     Document Type: Article

References (26)

1. For recent reviews of this area, see: (a) Shuttleworth, S. J.; Allin, S. M.; Wilson, R. D.; Nasturica, D. Synthesis 2000, 1035.
2. (b) Lindner, E.; Schneller, T.; Auer, F.; Mayer, H. A. Angew Chem., Int. Ed. 1999, 38, 2154.
3. (c) Shuttleworth, S. J.; Allin, S. M.; Sharma, P. K. Synthesis 1997, 1217.
4. (a) Comely, A. C.; Gibson, S. E.; Hales, N. J. J. Chem. Soc., Chem. Commun. 2000, 305.
5. (b) Leadbeater, N. E.; Scott, K. A.; Scott, L. J. J. Org. Chem. 2000, 65, 3231.
6. (c) Zhang, T. Y.; Allen, M. J. Tetrahedron Lett. 1999, 40, 5813.
7. (d) Buchmeiser, M. R.; Wurst, K. J. Am. Chem. Soc. 1999, 121, 11101.
8. (e) Ahmed, M.; Barrett, A. G. M.; Braddock, D. C.; Cramp, S. M.; Procopiou, P. A. Tetrahedron Lett. 1999, 40, 8657.
9. (f) Angelino, M. D.; Laibinis, P. E. Macromolecules 1998, 31, 7581.
10. (g) Fenger, I.; LeDrian, C. Tetrahedron Lett. 1998, 39, 4287.
11. (a) Rigby, J. H. In Advances in Cycloaddition; Harmata, M., Ed.; JAI Press: Greenwich, 1999; Vol. 6, pp 97-118.
12. (b) Rigby, J. H. Tetrahedron 1999, 55, 4521.
13. (c) Rigby, J. H. Acc. Chem. Res. 1993, 26, 579.
14. (a) Rigby, J. H.; Fiedler, C. J. Org. Chem. 1997, 62, 6106.
15. (b) Rigby, J. H.; Short, K. M.; Ateeq, H. S.; Henshilwood, J. A. J. Org. Chem. 1992, 57, 5290.
16. (a) Rigby, J. H.; Pigge, F. C. J. Org. Chem. 1995, 60, 7392.
17. (b) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495.
18. (c) Rigby, J. H.; Henshilwood, J. A. J. Am. Chem. Soc. 1991, 113, 5122.
19. (a) Evans, G. O.; Pittman, C. U.; McMillan, R.; Beach, R. T.; Jones, R. J. Organomet. Chem. 1974, 67, 295.
20. (b) Dumont, W.; Poulin, J.-C.; Dang, T.-Ph.; Kagan, H. B. J. Am. Chem. Soc. 1973, 95, 8295.
21. The amount of resin to be employed in these reactions is determined on the basis of the results of elemental analysis, which in this particular case indicated 2.08% Cr by weight (56% of maximum calculated chromium loading).
22. This compound has been prepared and fully characterized previously in our laboratory, see: ref 5b.
23. Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. D.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
24. Howell, J. A. S.; Palin, M. G.; McArdle, P.; Cunningham, D.; Goldschmidt, Z.; Gottlieb, H. E.; Herzoni-Langerman, D. Organometallics 1993, 12, 1694.
25. -1, respectively, which are quite similar to related nonresin-based arene dicarbonyl phosphine complexes: Bitterwolf, T. E. Polyhedron 1988, 7, 1377.
26. The electronic properties of arene ligands are known to exert a profound influence on the catalytic activities of chromium carbonyl complexes in other situations: Frankel, E. N.; Butterfield, R. O. J. Org. Chem. 1969, 34, 3930.