Disubstituted "K-region" arene oxides

The first syntheses of tri- and tetra-cyclic vic-disubstituted arene oxides are described. The general route to 9,10-dimethyl- and 9,10 - bis(p - chlorophenyl) - phenanthrene - 9,10 - oxide, and to 5,6 - diphenylbenzo[c]phenanthrene 5,6 - oxide, includes oxidation of the unsubstituted aromatic hydrocarbon to the K-region quinone followed by reaction with an alkyl- or aryl-magnesium bromide and treatment of the resulting trans-diol with dimethylformamide dimethylacetal. A previous report on the synthesis of a disubstituted chrysene oxide has been proved to be in error.