Conclusions
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1.
The quinone (IV) adds to pentacene in the 6.13 and 5.14 positions forming the isomeric adducts (III) and (V).
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2.
The ketoalcohol (IX) is extremely unstable: its hydroxycyclohexenone grouping is oxidized by atmospheric oxygen to the corresponding hydroxycyclohexadienone.
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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).
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4.
All the compounds described have been obtained for the first time.
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E. Clar, Ber.,64, 1676 (1931).
L. V. Antik, E. I. Klabunovskii, A. A. Balandin, and B. Ya. Karelli, Izv. AN SSSR, Ser. khim.,1964, 1470.
L. V. Antik, E. I. Klabunovskii, A. A. Balandin, B. V. Lopatin, and V. A. Petukhov, Izv. AN SSSR, Ser. khim.,1964, 1260.
A. A. Balandin, E. I. Klabunovskii, L. V. Antik, and R. Yu. Alieva, Dokl. AN SSSR,173, 825 (1967).
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1552–1559, July, 1967.
Deceased.
The authors express their thanks to V. A. Petukhov for recording the UV spectra.
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Antik, L.V., Klabunovskii, E.I., Balandin, A.A. et al. The synthesis and reactions of hexahydrodioxotetrabenzoanthrylentriptycene. Russ Chem Bull 16, 1497–1502 (1967). https://doi.org/10.1007/BF00905358
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DOI: https://doi.org/10.1007/BF00905358