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.
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.
Annelation in the quinoid portion of the molecule reduces the stability of the semiquinone.
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E. I. Klabunovskii, A. A. Balandin, and L. V. Antik, Izv. AN SSSR, Ser. Khim.,1964, 1785.
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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