96722-21-3Relevant articles and documents
Dimeric Naphthoquinones, XIV. - Intermediates of the cyclo-Trimerization of Naphthoquinone: Synthesis of Hydroxyheptastarphenequinones
Laatsch, Hartmut
, p. 605 - 619 (2007/10/02)
Dehydrogenation of heptastarphene-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-tetrahydroxyheptastarphene-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.