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- W2142383774 abstract "Dehydrierung von Hepta[2.2.2]starphen-5,6,11,12,17,18-hexaol (3a) mit einem Moläquivalent 1,4-Naphthochinon (1) führt fast quantitativ zu blaugrünem 5,12,17,18-Tetrahydroxyhepta-[2.2.2]starphen-6,11-chinon (4). Oxidation von 3a mit zwei Moläquivalenten 1 liefert dagegen statt des erwarteten Dichinons 5 ein 4/6-Gemisch. Aus dem gelben Tetraacetat 7b von 4 erhält man durch gezielte regioselektive Entacetylierung das blaue Triacetat 7c, das blaugrüne Diacetat 9, sein Isomeres 11 und unter Umlagerung rotes 14a. Ammonium-cer(IV)-nitrat oxidiert 7c zum Diacetat 8a des gesuchten Zwischenproduktes 5 der 3a-Dehydrierung. Silberoxid überführt 9 in das grüne Dichinon 10a und 11 in das violette Dichinon 12a, die sich in Pyridin unter Acylwanderung in 8a umlagern. Die Farben der Chinone lassen sich durch Donor-Acceptor-Wechselwirkungen erklären. Dimeric Naphthoquinones, XIV. – Intermediates of the cyclo- Trimerization of Naphthoquinone: Synthesis of Hydroxyhepta[2.2.2]starphenequinones Dehydrogenation of hepta[2.2.2]starphene-5,6,11,12,17,18-hexaol (3a) with one molar equivalent of 1,4-naphthoquinone (1) yields nearly quantitatively the blue-green 5,12,17,18-tetra-hydroxyhepta[2.2.2]starphene-6,11-quinone 4. Oxidation of 3a with two molar equivalents of 1 affords a 4/6 mixture of the expected diquinone 5. From the yellow tetraacetate 7b were obtained by regioselective deacetylation the blue triacetate 7c, the blue-green diacetate 9, its isomer 11 and, by rearrangement, red 14a. Oxidation of 7c yields 8a, the acetate of the intermediate 5 of the 3a dehydrogenation. 9 and 11 are oxidized by silver oxide to give the green diquinone 10a and the violet 12a, respectively, which both rearrange in pyridine by acyl migration forming 8a. The colour of the quinones is due to donor-acceptor interactions." @default.
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- W2142383774 date "1985-03-12" @default.
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- W2142383774 title "Dimere Naphthochinone, XIV. Zwischenstufen dercyclo-Trimerisierung von Naphthochinon: Synthese von Hydroxyhepta[2.2.2]starphenchinonen" @default.
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- W2142383774 doi "https://doi.org/10.1002/jlac.198519850322" @default.
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