Catalytic dehydrocyclization of 2-octylnaphthalene

  • N. I. Shuikin
  • L. A. Érivanskaya
  • Yang Ai-hsi
  • L. P. Romanova
Organic and Biological Chemistry


  1. 1.

    The transformations of 2-octylnaphthalene, 2-(2-methylcyclohexenyl)naphthalene, and 2-(2-ethylcyclohexenyl)naphthalene were investigated in presence of an alumia-chromium oxide catalyst at 450°.

  2. 2.

    2-Octylnaphthalene suffers dehydrocyclization both at the naphthalene nucleus with formation of phenanthrene (mainly) and anthracene, and at a carbon atom of the alkyl group with formation of 11H-benzo[a]fluorene, 11H-benzo[b]fluorene, benz[a]anthracene, and chrysene.

  3. 3.

    The dehydrocyclization of 2-(2-methylcyclohexenyl)naphthalene gave 11H-benzo[a]fluorene and 11H-benzo[b]fluorene, and the dehydrocyclization of 2-(2-ethylcyclohexenyl)naphthalene gave 11H-benzo[a]fluorene, 11H-benzo[b]fluorene, 11-methyl-11H-benzo[a]fluorene, benz[a]anthracene, and chrysene.



Oxide Carbon Atom Fluorene Naphthalene Alkyl Group 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Literature cited

  1. 1.
    N. I. Shuikin, L. A. Érivanskaya, N. L. Komissarova, and Yang Ai-hsi, Izv. AN SSSR. Otd. khim. n. 328 (1962).Google Scholar
  2. 2.
    I. L. Kotlyarevskii and M. S. Shvartsberg, Zh. obshch. khimii29, 2639, 3255 (1959).Google Scholar
  3. 3.
    N. I. Shuikin, L. A. Érivanskaya and Yang Ai-hsi, Dokl. AN SSSR133, 1125 (1960).Google Scholar
  4. 4.
    Huang-Minlon, J. Amer. Chem. Soc.68, 2487 (1946).Google Scholar
  5. 5.
    A. S. Bailey, G. B. Pickering, and J. C. Smith, J. Inst. Petrol.35, 103 (1949).Google Scholar
  6. 6.
    Buu-Hoi and P. Gagniant, Bull. Soc. chim. France12, 307 (1945).Google Scholar
  7. 7.
    H. Luther and G. Wächter, Chem. Ber.82, 161 (1949).Google Scholar
  8. 8.
    M. S. Newman and P. H. Wise, J. Amer. Chem. Soc.63, 2847 (1941).Google Scholar
  9. 9.
    R. A. Friedel, M. Orchin, and L. Reggel, J. Amer. Chem. Soc.70, 199 (1948).Google Scholar
  10. 10.
    R. A. Friedel and M. Orchin, Ultraviolet Spectra of Aromatic Compounds. N. Y., (1951).Google Scholar
  11. 11.
    V. R. Skvarchenko, Ling Weng-lien and R. Ya. Levina, Zh. obshch. khimii31, 383 (1961).Google Scholar
  12. 12.
    C. F. Koelsch, J. Amer. Chem. Soc.55, 3887 (1933).Google Scholar
  13. 13.
    E. Clar, Aromatische Kohlenwasserstoffe, Berlin, 174 (1952).Google Scholar
  14. 14.
    J. W. Cook and C. L. Hewett, J. Chem. Soc. 374, 1737 (1934).Google Scholar
  15. 15.
    G. M. Badger, J. Chem. Soc. 535 (1941).Google Scholar
  16. 16.
    R. Weitenböck and H. Lieb, Monatsh33, 549 (1912).Google Scholar

Copyright information

© Consultants Bureau 1964

Authors and Affiliations

  • N. I. Shuikin
    • 1
  • L. A. Érivanskaya
    • 1
  • Yang Ai-hsi
    • 1
  • L. P. Romanova
    • 1
  1. 1.M. V. Lomonosov Moscow State UniversityUSSR

Personalised recommendations