Oxidations by methyl(trifluoromethyl)dioxirane. 4. Oxyfunctionalization of aromatic hydrocarbons

By using the title dioxirane (1a), naphthalene (2), phenanthrene (3), and anthracene (4) have been converted into anti-naphthalene-1,2;3,4-dioxide (2?), phenonthrene-9,10-oxide (3?), and anthraquinone (4?), respectively, in high yield and under mild conditions. However, the transformation of pyrene (5) - an higher homologue of the polycyclic aromatic hydrocarbon series - into the corresponding arene oxide was found to procced much less effectively.