Attempt 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 |