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Synthesis and polarographic reduction of dihydrodioxodibenzonaphthotriptycene

Conclusions

  1. 1.

    11,12,15,16-Tetrahydro-12,15-dioxo-2,3;6,7-dibenzo-13,14;2,3-naphthotriptycene (IV), 2,15-dihydro-12,15-dioxo-2,3;6,7-dibenzo-13,14; 2,3-naphthotriptycene (III), and the corresponding hydroquinone (I) were produced for the first time; the latter is readily oxidized and characterized in the form of the diacetate.

  2. 2.

    The quinone (III) is reduced in dimethylformamide medium against a background of 0.1 N KNO3, forming two waves with half-wave potentials 814 and 1330 mV.

  3. 3.

    Annelation in the quinoid portion of the molecule reduces the stability of the semiquinone.

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Literature cited

  1. 1.

    E. I. Klabunovskii, A. A. Balandin, and L. V. Antik, Izv. AN SSSR, Ser. Khim.,1964, 1785.

  2. 2.

    E. I. Klabunovskii, R. Yu. Mamedzade, L. V. Antik, I. V. Gorelik, and L. A. Gorskaya, Izv. AN SSSR, Ser. Khim.,1964, 1554.

  3. 3.

    L. V. Antik, E. I. Klabunovskii, A. A. Balandin, and Ya. Karele, Izv. AN SSSR, Ser. Khim.,1964, 1470.

  4. 4.

    L. V. Antik, E. M. Klabunovskii, A. A. Balandin, B. V. Lopatin, and V. A. Petukhov, Izv. AN SSSR, Ser. Khim.,1964, 1260.

  5. 5.

    M. V. Gorelik, Zh. Obshch. Khimii,29, 2852 (1959).

  6. 6.

    G. Markus, Science,119, 324 (1954).

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 306–309, February, 1967

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Mamedzade, R.Y., Klabunovskii, E.I., Antik, L.V. et al. Synthesis and polarographic reduction of dihydrodioxodibenzonaphthotriptycene. Russ Chem Bull 16, 293–296 (1967). https://doi.org/10.1007/BF00912431

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Keywords

  • Quinone
  • Hydroquinone
  • Dimethylformamide
  • Diacetate
  • KNO3