Reactions of quinones with aromatic ethers. Part VII. Triphenylene-1,4 : 5,8-diquinones from reactions of veratrole or 3,4-dimethoxyphenylbenzoquinones with benzoquinones
Abstract
Veratrole reacts with 1,4-benzoquinone in the presence of aluminium chloride to form 10,11-dimethoxytriphenylene-1,4:5,8-diquinone. Related products result when 2-chloro- and 2,3-dichloro-1,4-benzoquinone are used. 3,4-Dimethoxyphenyl-1,4-benzoquinone reacts in a similar manner with unsubstituted, 2-methyl-, 2-chloro-, and 2,3-dichloro-1,4-benzoquinone, and with itself. The structures of the diquinones follow from their spectroscopic properties and their conversion into the corresponding triphenylene-1,4,5,8-tetrayl tetra-acetates by reductive acetylation.