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EnglishAttempt 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.
| Autori interni: | ||
| Autori: | KROHN K; ASLAN A; AHMED I; PESCITELLI G; FUNAIOLI T | |
| Titolo: | Novel 1,4,5,8-Phenanthrenediquinones and Unusual Deoxygenation using Trimethylsilyl Iodide | |
| Anno del prodotto: | 2009 | |
| Digital Object Identifier (DOI): | 10.1002/ejoc.200900666 | |
| Appare nelle tipologie: | 1.1 Articolo in rivista |
File in questo prodotto:
http://hdl.handle.net/11568/203619
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