Triscyclopenta[cd,fg,jk]pyrene: another congener of the externally cyclopenta-fused pyrene series

(Note: The full text of this document is currently only available in the PDF Version )

Martin Sarobe, Remco W. A. Havenith, Leonardus W. Jenneskens and Remco W. A. Havenith


Abstract

Flash vacuum thermolysis of 1,3,6-tris(1-chloroethenyl)pyrene 5 between 900–950 °C gave the thermally labile triscyclopenta[cd,fg,jk]pyrene 1; in line with the ‘conjugated circuits model’ and supported by IGLO III//RHF/6-31G calculations, all hydrogen atoms of 1 are additionally shielded by 0.4–0.9 ppm (1H NMR).


References

  1. M. Sarobe, J. W. Zwikker, J. D. Snoeijer, U. E. Wiersum and L. W. Jenneskens, J. Chem. Soc., Chem. Commun., 1994, 89 RSC.
  2. For arecent review: U. E. Wiersum and L. W. Jenneskens, in Gas Phase Reactions in Organic Synthesis, ed. Y. Vallée, Gordon and Breach, Amsterdam, The Netherlands, 1997, ch. 3, pp. 143–194 Search PubMed.
  3. H. Bockhorn, F. Fetting and H. W. Wenz, Ber. Bunsenges. Phys. Chem., 1983, 87, 1067 Search PubMed and references cited therein.
  4. M. Sarobe, S. Flink, L. W. Jenneskens, B. L. A. van Poecke and J. W. Zwikker, J. Chem. Soc., Chem. Commun., 1995, 2415 RSC.
  5. L. T. Scott and A. Necula, J. Org. Chem., 1996, 61, 386 CrossRef CAS.
  6. A. L. Lafleur, J. B. Howard, K. Taghizadeh, E. F. Plummer, L. T. Scott, A. Necula and K. C. Swallow, J. Phys. Chem., 1996, 100, 17421 CrossRef CAS and references cited therein.
  7. J. R. Platt, J. Chem. Phys., 1954, 22, 1448 CAS.
  8. M. Kataoka, Tetrahedron, 1997, 53, 12 875 CrossRef CAS.
  9. M. Randić, Tetrahedron, 1977, 33, 1905 CrossRef CAS and references cited therein.
  10. R. F. C. Brown, K. J. Coulston and F. W. Eastwood, Tetrahedron Lett., 1996, 37, 6819 CrossRef.
  11. S. E. Stein and A. Fahr, J. Phys. Chem., 1985, 89, 3714 CrossRef CAS.
  12. U. E. Fleischer, W. Kutzelnigg, P. Lazzaretti and V. Mülhenkamp, J. Am. Chem. Soc., 1994, 116, 5298 CrossRef CAS and references cited therein.
  13. P. von Rague Schleyer, C. Maerker, A. Dransfeld, H. Jiao and N. J. R. van Eikema Hommes, J. Am. Chem. Soc., 1996, 118, 6317 CrossRef CAS.
  14. E. Clar, in Polycyclic Hydrocarbons, Academic Press, London, 1964 Search PubMed.
  15. W. Ried and V. B. Saxema, Angew. Chem., 1968, 80, 366.
  16. P. H. Gore, in Friedel and Crafts and Related Reactions, ed. G. A. Olah, Interscience, New York, vol. III, 1964, pp. 74–80 Search PubMed.
Click here to see how this site uses Cookies. View our privacy policy here.