30266-58-1Relevant articles and documents
Superoxide Oxidation: A Novel Route to Aromatic 1,2-Dicarboxylic Acids
Sotiriou, Chariklia,Lee, Wenni,Giese, Roger W.
, p. 2159 - 2164 (2007/10/02)
Potassium superoxide in aprotic media, in the presence of 18-crown-6 ether, effects a novel and mild oxidative cleavage of quinones, cyclic alcohols, and ketones fused to various aromatic hydrocarbons.Aromatic 1,2-dicarboxylic acids are obtained as major products, with highest yields in dimethylformamide, under oxygen or air.For example, the yield of pyrene-1,2-dicarboxylic acid is 82percent from 9,10-dihydrobenzopyren-7(8H)-one and 88percent from benzopyrene-7,8-dione.Minor side products include aromatic tetrones and 3-(2-carboxyaryl)propionic or 3-(2-carboxyaryl)propenoic acid, which provide mechanistic insights.