Partially benzoanellated centrohexaquinanes: Oxidative degradation of centropolyindanes by using ruthenium(VIII) oxide and ozone

Gestmann D, Pritzkow H, Kuck D (1996)
LIEBIGS ANNALEN (9): 1349-1359.

Journal Article | Published | English

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The oxidative degradation of benzo nuclei of various higher centropolyindanes with ruthenium(VIII) oxide or ozone was studied to further explore the chemistry of partially benzo-anellated centrohexaquinanes. Besides the two tribenzotriquinacenes 12 and 15 which were used as model substrates for oxidation with Ru-VIII, centrohexaindane 1 was converted to the corresponding centrohexacyclic diketone 19 by using either RuO4 in stoichiometric amounts or O-3 in dichloromethane/pyridine. Subsequent Wolff-Kishner reduction of 19 gave pentabenzohexaquinane 4. Correspondingly, tribenzo-centrohexaquinane 2 was degraded by sequential ozonolysis/reduction to the C-2v-symmetrical dibenzocentrohexaquinane and 10 and monobenzocentrohexaquinane 11 in low yields (8-9% in each sequence). Due to the low efficiency of the ozonolyses, the parent centrohexaquinane 3 has remained elusive, yet. The deeply red centrohexacyclic 1,2-diketone 19 was subjected to single-crystal X-ray structural analysis and found to bear an almost perfectly syn-coplanar alpha-dicarbonyl chromophore with a strong and extremely low-energy UV/Vis absorption (lambda(max) = 512 and 531 nm).
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Gestmann D, Pritzkow H, Kuck D. Partially benzoanellated centrohexaquinanes: Oxidative degradation of centropolyindanes by using ruthenium(VIII) oxide and ozone. LIEBIGS ANNALEN. 1996;(9):1349-1359.
Gestmann, D., Pritzkow, H., & Kuck, D. (1996). Partially benzoanellated centrohexaquinanes: Oxidative degradation of centropolyindanes by using ruthenium(VIII) oxide and ozone. LIEBIGS ANNALEN(9), 1349-1359.
Gestmann, D., Pritzkow, H., and Kuck, D. (1996). Partially benzoanellated centrohexaquinanes: Oxidative degradation of centropolyindanes by using ruthenium(VIII) oxide and ozone. LIEBIGS ANNALEN, 1349-1359.
Gestmann, D., Pritzkow, H., & Kuck, D., 1996. Partially benzoanellated centrohexaquinanes: Oxidative degradation of centropolyindanes by using ruthenium(VIII) oxide and ozone. LIEBIGS ANNALEN, (9), p 1349-1359.
D. Gestmann, H. Pritzkow, and D. Kuck, “Partially benzoanellated centrohexaquinanes: Oxidative degradation of centropolyindanes by using ruthenium(VIII) oxide and ozone”, LIEBIGS ANNALEN, 1996, pp. 1349-1359.
Gestmann, D., Pritzkow, H., Kuck, D.: Partially benzoanellated centrohexaquinanes: Oxidative degradation of centropolyindanes by using ruthenium(VIII) oxide and ozone. LIEBIGS ANNALEN. 1349-1359 (1996).
Gestmann, D, Pritzkow, H, and Kuck, Dietmar. “Partially benzoanellated centrohexaquinanes: Oxidative degradation of centropolyindanes by using ruthenium(VIII) oxide and ozone”. LIEBIGS ANNALEN 9 (1996): 1349-1359.
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