Catalytic Chromium(0)-Promoted [6π + 4π] Cycloaddition Reactions

Journal of Organic Chemistry

Volumn 62, Issue 18, 1997, Pages 6106-6107

  Rigby, James H ^a   Fiedler, Christian ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001556437     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9707444     Document Type: Article

References (19)

1. (a) Rigby, J. H. Acc, Chem. Res. 1993, 26, 579.
2. (b) Chafee, K.; Huo, P.; Sheridan, J. B.; Barbieri, A,; Aistars, A.; Lalancette, R. A.; Ostranden, R. L.; Rheingold, A. L. J. Am. Chem. Soc. 1995, 117, 1900.
3. (c) Rigby, J. H.; Rege, S. D.; Sandanayaka, V. P.; Kirova, M. J. Org. Chem. 1996, 61, 842.
4. (d) Rigby, J. H.; Warshakoon, N. C.; Heeg, M. J. J. Am. Chem. Soc. 1996, 118, 6094,
5. (e) Chen, W.; Chafee, K.; Chung, H.-J.; Sheridan, J. B. J. Am. Chem. Soc. 1996, 118, 9980.
6. (a) Rigby, J. H.; Pigge, F. C. J. Org. Chem. 1995, 60, 7392.
7. (b) Rigby, J. H.; Niyaz, N. M.; Short, K.; Heeg, M. J. J. Org. Chem. 1995, 60, 7720.
8. (c) Rigby, J. H.; Warshakoon, N. C. J. Org. Chem. 1996, 61, 7644.
9. For a review of [6 + 4] cycloaddition reactions, see: Rigby, J. H. Org. Reac. (N.Y.) 1997, 49, 331.
10. (a) Rigby, J. H.; Short, K. M.; Ateeq, H. S.; Henshilwood, J. A. J. Org. Chem. 1992, 57, 5290.
11. (b) Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Henshilwood, J. A.; Short, K. M.; Sugathapala, P. M. Tetrahedron 1993, 49, 5495.
12. 3" catalysts have been invoked in the 1,4-reduction of dienes in coordinating solvents: Yagupsky, G.; Cais, M. Inorg. Chim. Acta 1975, 12, L27.
13. 3+ + 3e → Cr -0.744
14. All cycloadducts have been prepared and fully characterized previously: Rigby, J. H.; Ateeq, H. S.; Charles, N. R.; Cuisiat, S. V.; Ferguson, M. P.; Henshilwood, J. A.; Krueger, A. C.; Ogbu, C. O.; Short, K. M.; Heeg, M. J. J. Am. Chem. Soc. 1993, 115, 1382.
15. General Procedure for Conducting Catalytic [6π + 4π] Cycloaddition Reactions: A Carius tube is flushed with dry nitrogen and then charged with the appropriate Cr(0) precatalyst (0,1 equiv), freshly distilled solvent (10-20 mL), magnesium powder (0.1 equiv), cycloheptatriene (1 equiv), and the diene (10-12 equiv). This mixture was carefully degassed using the freeze-pump-thaw technique, and the tube was then sealed and heated at 140°C for 2-5 days. After cooling to room temperature, the resulting suspension was filtered through Celite. The filtrate solvent was removed in vacuo, and column chromatography afforded the product.
16. (a) Abel, E.; Bennett, M. A.; Burton, R.; Wilkinson, G. J. Chem. Soc, 1958, 4559.
17. (b) Tate, D. P.; Knipple, W. R.; Augl, J. M. Inorg. Chem. 1962, 1, 437.
18. (a) Fischer, E. O.; Oefele, K.; Essler, H.; Frölich, W.; Mortensen, J. P.; Semmlinger, W. Chem. Ber. 1958, 91, 2763.
19. (b) Desobry, V.; Kündig, E. P. Helv. Chim. Acta 1981, 64, 1288.