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Synthesis and reactions of 6,13-dihydro-6,13[2′, 3′]-naphthalenopentacene-5,14-dione

  • L. V. Antik
  • E. I. Klabunovskii
  • A. A. Balandin
  • B. V. Lopatin
  • V. A. Petukhov
Organic and Biological Chemistry
  • 28 Downloads

Summary

  1. 1.

    1,4-Naphthoquinone undergoes diene condensation with pentacene both in the 6, 13-positions (middle ring of pentacene) and in the 5,14-positions (second ring of pentacene). This results in the formation of two adducts: 5a,6,13,13a-tetrahydro-6,13[2′,3′]-naphthalenopentacene-5,14-dione (III) and 5a,6,15,15a-tetrahydro-6,15-o-benzenohexacene-5-16-dione (IV). The structures of the isomers isolated were confirmed by spectroscopic data.

     
  2. 2.

    The following were synthesized for the first time: the adducts (III) and (IV), 6,13-dihydro-6,13[2′,3′]-napthalenopentacene-5,14-dione (II),6,13-dihydro-6,13[2′,3′]-naphthalenopentacene-5,14-diol (V), and the corresponding quinhydrone (VIII); the hydroquinone (V) was characterized also as its diacetyl derivative (VI).

     
  3. 3.

    Increase in the number of linearly annelated rings in the hydrocarbon part of the bridged hydroquinone 5,12-dihydro-5,12-o-benzenonaphthacene-6,11-diol (VII) so as give the hydroquinone (V) leads to a more stable molecule.

     

Keywords

Hydrocarbon Adduct Diene Diol Dione 
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.

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Literature cited

  1. 1.
    E. Clar, Aromatische Kohlenwasserstoffe, 2 Aufl. Berl. Spr. Verlag (1952).Google Scholar
  2. 2.
    W. Theilacker, U. Berger-Brose, and K. Beyer, Chem. Ber.,93, 1658 (1960).Google Scholar
  3. 3.
    A. A. Balandin, E. I. Klabunovskii, and L. V. Antik, Izv. AN SSSR. Old. Khim. N.,1961, 2189.Google Scholar
  4. 4.
    E. I. Klabunovskii, A. A. Balandin, and L. V. Antik, Izv. AN SSSR. Ser. Khim., 1964 (in Press).Google Scholar
  5. 5.
    E. I. Klabunovskii, L. V. Antik, and N. A. Ezerskaya, Izv. AN SSSR. Otd. Khim. N.,1962, 1877; E. I. Klabunovskii, L. V. Antik, and A. A. Balandin, Izv. AN SSSR. Ser. Khim.,1964, 789.Google Scholar
  6. 6.
    E. Clar and F. John, Ber.,63, 2968 (1930).Google Scholar
  7. 7.
    C. Hurd and L. Juel, J. Amer. Chem. Soc.,77, 601 (1965).Google Scholar
  8. 8.
    F. Cramer, Clathrate Compounds (Russian translation), IL, M., 1958, p. 153.Google Scholar
  9. 9.
    M. C. Joisien and N. Euson, Bull. Soc. chim. France,19, 389 (1952).Google Scholar
  10. 10.
    J. Grove and H. Willis, J. Chem. Soc.,1951, 877.Google Scholar
  11. 11.
    G. G. Connon and I. B. Sutherland, Spectroehim. Acta,4, 373 (1951).Google Scholar
  12. 12.
    Application of Spectroscopy in Chemistry, Edited by West (Russian translation), IL, M.,1959, p. 389Google Scholar
  13. 13.
    H. E. Zimmerman, J. Amer. Chem. Soc.,82, 1514 (1960).Google Scholar
  14. 14.
    P. D. Bartlett and E. S. Lewis, J. Amer. Chem. Soc.,72, 1005 (1950).Google Scholar
  15. 15.
    E. Clar, Chem. Ber.82, 495 (1949).Google Scholar
  16. 16.
    E. Clar and C. Marschalk, Bull. (5),17, 444 (1950).Google Scholar

Copyright information

© Consultants Bureau Enterprises, Inc. 1965

Authors and Affiliations

  • L. V. Antik
    • 1
  • E. I. Klabunovskii
    • 1
  • A. A. Balandin
    • 1
  • B. V. Lopatin
    • 1
  • V. A. Petukhov
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of SciencesUSSR

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