The synthesis and reactions of hexahydrodioxotetrabenzoanthrylentriptycene

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

Conclusions

  1. 1.

    The quinone (IV) adds to pentacene in the 6.13 and 5.14 positions forming the isomeric adducts (III) and (V).

     
  2. 2.

    The ketoalcohol (IX) is extremely unstable: its hydroxycyclohexenone grouping is oxidized by atmospheric oxygen to the corresponding hydroxycyclohexadienone.

     
  3. 3.

    On being heated to ∼ 140° (at a residual pressure of nitrogen of 5 mm or in solution in acetic anhydride) the ketoalcohol (XI) undergoes a rearrangement into the corresponding hydroquinone (in the latter case, with simultaneous acetylation).

     
  4. 4.

    All the compounds described have been obtained for the first time.

     

Keywords

Oxygen Nitrogen Acetic Adduct Anhydride 

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Literature cited

  1. 1.
    L. V. Antik, R. Yu. Mamedzade, E. I. Klabunovskii, and A. A. Balandin, Izv. AN SSSR, Ser. khim.,1967, 568.Google Scholar
  2. 2.
    E. Clar, Ber.,64, 1676 (1931).Google Scholar
  3. 3.
    L. V. Antik, E. I. Klabunovskii, A. A. Balandin, and B. Ya. Karelli, Izv. AN SSSR, Ser. khim.,1964, 1470.Google Scholar
  4. 4.
    L. V. Antik, E. I. Klabunovskii, A. A. Balandin, B. V. Lopatin, and V. A. Petukhov, Izv. AN SSSR, Ser. khim.,1964, 1260.Google Scholar
  5. 5.
    A. A. Balandin, E. I. Klabunovskii, L. V. Antik, and R. Yu. Alieva, Dokl. AN SSSR,173, 825 (1967).Google Scholar
  6. 6.
    E. Blout, M. Fields, and R. Karplus, J. Amer. Chem. Soc.,70, 194 (1948).Google Scholar

Copyright information

© Consultants Bureau 1968

Authors and Affiliations

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

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