Chemistry of quinones. Part II. Some base-catalysed reactions of alkylanthraquinones
Abstract
When 1- and 2-methyl-, 2-ethyl-, and 2-isopropyl-anthraquinone are treated with the reagent formed by adding water (3 equiv.) to potassium t-butoxide (10 equiv.) in 1,2-dimethoxyethane, the main reaction is oxidation to give dehydro-dimers. 2-Methylanthraquinone, for example gives 1,2-di(anthraquinon-2-yl)ethylene. 2-t-Butyl-anthraquinone, however, is cleaved in high yield when treated with the same reagent giving a mixture of benzolc and 3- and 4-t-butylbenzoic acids.