Abstract
The reaction of 4,5-didehydroacenaphthene with phencyclone yields the title compound, a stable dibenzo-fused norbornadienone (8). The X-ray structure of8 is presented and compared with the structure predicted from a MM3, PM3, and a MMX calculation. Thermal decomposition of 8 produces, 7,16-diphenylcyclopenta[d,e]tribenzo[a,h,j]anthracene (9), a hydrocarbon that is computed to have a significantly twisted polycyclic aromatic skeleton with 19 kcal/mole of strain energy.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Miki, S.; Kagawa, H.; Matsuo, K.; Kobayashi, O.; Yoshida, M.; Yoshida, Z.Tetrahedron 1992,48, 1567–1572.
Meinwald, J.; Miller, E. G.Tetrahedron Lett. 1961, 253–255.
Platter, M. J.; Rees, C. W.J. Chem. Soc. Perkin Trans. 1 1991, 317–321.
Warrener, R. N.; Russell, R. A.; Pitt, I. G.J. Chem. Soc. Chem. Commun. 1974, 1675–1676.
Irie, T.; Tanida, H.J. Org. Chem. 1979,44, 1002–1003.
Landesberg, J. M.; Sieczkowski, J.J. Am. Chem. Soc. 1971,93, 972–980.
Birney, D. M.; Wiberg, K. B.; Berson, J. A.J. Am. Chem. Soc. 1988,110, 6631–6642.
Plummer, B. F.; Singleton, S. F.J. Phys. Chem. 1989,93, 5515–5520.
Plummer, B. F.; Russell, S. J.; Reese, W. G.; Watson, W. H.; Krawiec, M.J. Org. Chem. 1991,56, 3219–3223.
Plummer, B. F.Polycycl. Arom. Compounds 1993,3, 77–88.
Plummer, B. F.; Steffen, L. K.; Herndon, W. H.Struct. Chem. 1993,4, 279–285.
Plummer, B. F.; Reese, W. G.; Watson, W. H.; Kashyep, R. P.Struct. Chem. 1993,4, 53–57.
Plummer, B. F.; Steffen, L. K.; Braley, T. L.; Reese, W. G.; Zych, K.; Van Dyke, G.; Tulley, B.J. Am. Chem. Soc. 1993,115, 11542–11551.
Plummer, B. F.Polycycl. Arom. Compounds 1994,4, 25–39.
Gilbert, K. E. Serena Software: Bloomington, IN.
Allinger, N. L.; Geise, H. J.; Pyckhout, W.; Paquette, L. A.; Gallucci, J. C.J. Am. Chem. Soc. 1989,111, 1106–1114.
Stewart, J. J. P.J. Comp.-Aided Mol. Design 1990,4, 1.
Currey, J. A. Senior Honors Thesis, Trinity University,1993.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Plummer, B.F., Currey, J.A., Russell, S.J. et al. The synthesis and X-Ray crystallographic analysis of a stable norbornadienone: 17-Oxo-7,16-methano-7,16-diphenylcyclopenta[d,e]tribenzo[a,h,j]anthracene. Struct Chem 6, 167–173 (1995). https://doi.org/10.1007/BF02286444
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02286444