Abstract
AbstractAttempt for aryl methyl ether cleavage of 5,8‐dimethoxy‐1,4‐phenanthrenequinone (4) with boron trichloride or tribromide resulted in the halogenation of the quinone double bond to form 5a,b. Surprisingly, reaction of dimethyl ether 4 with trimethylsilyl iodide afforded the phenanthrenediquinone 6, whereas deoxygenation to 8 and 9 occurred by reaction of trimethylsilyl iodide with derivative 7. The phenanthrenediquinones 6 and 10 were obtained nearly quantitatively from 4 and 7 by using ceric ammonium nitrate as the oxidant. The cyclic voltammograms of the phenanthrenediquinones 6 and 10 were studied and rationalized by Hückel Molecular Orbital calculations. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
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