Synthesis of a new C32H12 Bowl-Shaped aromatic hydrocarbon

Tetrahedron Letters

Volumn 38, Issue 5, 1997, Pages 741-744

  Clayton, Mark D ^a   Rabideau, Peter W ^a  

^a LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; DRUG IDENTIFICATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PYROLYSIS;

EID: 0031037058     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02450-1     Document Type: Article

References (22)

1. For recent reviews on bowl-shaped, fullerene related hydrocarbons, see (a) Siegel, J. S.; Seiders, T. J. Chem. in Britain 1995, 313.
2. (b) Faust, R. Angew. Chem. Internat. Ed. Engl. 1995, 34, 1429.
3. Rabideau, P. W.; Sygula, A. in Advances in Theoretically Interesting Molecules, Vol. 3, Thummel, R. P., Ed. Jai Press Inc., Greenwich, CT, 1995; pp 1-36.
4. Rabideau, P. W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235.
5. (e) Scott, L. T. Pure Appl. Chem. 1996, 68, 291.
6. Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 381. See also, Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1971, 93, 1730.
7. Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1966, 88, 381. See also, Barth, W. E.; Lawton, R. G. J. Am. Chem. Soc. 1971, 93, 1730.
8. (a) Scott, L. T.; Hashemi, M. M.; Meyer, D. T.; Warren, H. B. J. Am. Chem. Soc. 1991, 113, 7082.
9. (b) See also, Borchardt, A.; Fuchicello, A.; Kilway, K. V.; Baldridge, K. K.; Siegel, J. S. J. Am. Chem. Soc. 1992, 114, 1921.
10. Abdourazak, A. H.; Sygula, A.; Rabideau, P. W. J. Am. Chem. Soc. 1993, 115, 3010.
11. Sygula, A.; Abdourazak, A. H.; Rabideau, P. W. J. Am. Chem. Soc. 1996, 118, 339.
12. Rabideau, P. W.; Abdourazak, A. H.; Folsom, H. E.; Marcinow, Z.; Sygula, A.; Sygula, R. J. Am. Chem. Soc. 1994, 116, 7891.
13. Abdourazak, A. H.; Marcinow, Z.; Sygula, A; Sygula, R.; Rabideau, P. W. J. Am. Chem. Soc., 1995, 117, 6410.
14. (a) Loguercio, D. Ph.D. Thesis, UCLA, Los Angeles, CA, 1988.
15. (b) Faust, R.; Vollhardt, K. P. C. J. Chem. Soc., Chem. Commun. 1993, 1471.
16. Narahari, G. H.; Jemmis, E. D.; Mehta, G.; Shah, S. R. J. Chem. Soc., Perkin Trans. 2 1993, 1867.
17. Formed in trace amounts. See Hagen, S.; Christoph, H.; Zimmerman, G. Tetrahedron, 1995, 51, 6961.
18. Scott, L. T.; Bratcher, M. S.; Hagen, S. J. Am. Chem. Soc. 1996, 118, 8743.
19. Bennett, M. A.; Neumann, H. Aust. J. Chem. 1980, 33, 1251.
20. 2O: C, 63.07; H, 2.74. Found: C, 62.84; H, 2.65.
21. 2: C, 68.35; H, 3.23. Found: C, 68.05; H, 3.55.
22. 13C NMR (300 MHz), 152.45, 150.34, 149.08, 141.48, 140.92, 140.56, 138.53, 134.18, 133.57, 128.87, 127.50, 126.92, 126.23, 125.85, 123.54, 119.61. HRMS required 396.0939. Found 396.0930.