Generation of four five-membered rings in a one pot process. Studies directed toward the synthesis of dicyclopenta[a,d]pentalene via the tandem Pauson-Khand reaction

Tetrahedron Letters

Volumn 37, Issue 40, 1996, Pages 7185-7188

  Van Ornum, Scott G ^a   Cook, James M ^a  

^a UNIVERSITY OF WISCONSIN MILWAUKEE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030607160     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01634-6     Document Type: Article

References (20)

1. 1. Fu, X.; Cook, J.M. Aldrichimica Acta. 1992, 25, 42.
2. 2. Gupta, A.K.; Fu, X.; Snyder, J.P.; Cook, J.M. Tetrahedron 1991, 47, 3665.
3. 3. (a) Toyota, A.; Nakajima, T. Tetrahedron 1981, 37, 2572.
4. (b) Nakajima, T.; Toyota, A.; Kataoka, M. J. Am. Chem. Soc. 1982, 104, 5610.
5. 4. Hess, Jr., B. A.; Schaad, L.J. J. Org. Chem. 1971, 36, 3418.
6. 5. Koehler, K.; Van Ornum, S.G.; Cook, J.M. unpublished results. Energies for 1 and 2 were calculated using Gaussian 94 (Rev B.2) at the 6-31G* basis set.
7. 6. Stowasser, B.; Hafner, K. Angew. Chem. Int. Ed. Engl. 1986, 25, 466.
8. 7. Lannoye, G.; Sambasivarao, K.; Wehrli, S.; Weiss, U.; Cook, J.M. J. Org. Chem. 1988, 53, 2327.
9. 8. (a) Khand, I. U.; Knox, G. R.; Pauson, P.L.; Watts, W. E. J. Chem. Soc., Chem. Commun. 1971, 36.
10. (b) Khand, I. U.; Knox, G. R.; Pauson, P.L.; Watts, W. E. J. Chem. Soc., Perkin Trans. I 1973, 975.
11. 9. Krafft, M. E.; Scott, I. L.; Romero, R. H.; Feibelmann, S.; Van Pelt, C. E. J. Am. Chem. Soc. 1993, 115, 7199
12. 10. Schore, N. E. Org. React. John Wiley & Sons, Ed. Paquette, L. A. Academic Press, N.Y. 1991, 40, 1.
13. 11. Gybin, A. S.; Smit, W. A.; Caple, R.; Veretenov, A. L.; Shashkov, A. S.; Vorontsova, L. G.; Kurella, M.G.; Chertkov, V. S.; Carapetyan, A. A.; Kosnikov, A. Y.; Alexanyan, M. S.; Lindeman, S. V.; Panov, V. N.; Maleev, A. V.; Struchkov, Y. T.; Sharpe, S. M. J. Am. Chem. Soc. 1992, 114, 5555.
14. 12. Battersby, A.R.; Westwood, W. J. Chem. Soc. Perkin. Trans. I 1987, 1679.
15. 13. Davis, F. A.; Haque, M. S.; Ulatowski, T. G.; Towson, J. C. J. Org. Chem. 1986, 51, 2404.
16. 14. Huet, F.; Pellet, M.; Conia, J.M. Synthesis, 1979, 33.
17. 15. Rosini, C.; Scamuzzi, S.; Focati, M. P.; Salvadori, P. J. Org. Chem. 1995, 60, 8289.
18. 16. Thommen, M.; Veretenov, A. L.; Guidetti-Grept, R.; Keese, R. Helv. Chem. Acta. 1996, 79, 461.
19. 17. Shambayati, S.; Crowe, W. E.; Schreiber, S. L. Tetrahedron Lett. 1990, 31, 5289.
20. 3): δ 208.73, 208.17, 182.90, 181.48, 127.14, 126.65, 117.60, 104.13, 89.21, 44.14, 43.58, 42.96, 42.64, 42.39, 41.91, 28.62, 28.02 MS(CI) 287 (M+1, 100%), 271(70), 258(17), 243(15), 229(11), 211(7).