Synthesis of diarene oxides of benz[a]anthracene, chrysene and benzo[c]phenanthrene

A three-step synthetic route to the diarene oxides 5,6;10,11-diepoxy-5,6,10,11-tetrahydrobenz[a]anthracene 18, 5,6;8,9-diepoxy-5,6,8,9-tetrahydrobenz[a]anthracene 22, 3,4;5,6-diepoxy-3,4,5,6-tetrahydrochrysene 26 and 3,4;7,8-diepoxy-3,4,7,8-tetrahydrobenzo[c]-phenanthrene 30, from the corresponding trans-bromo acetate precursors 15, 19, 23, and 27 has been developed. Acid-catalysed isomerization studies to isomeric mixtures of phenols have been carried out.