# Oxidation of polycyclic aromatic compounds using KMnO4

How is tetracene oxidised by $$\ce{KMnO4}?$$ It appears that the product is a white solid with a benzene ring inside.

What is the reaction mechanism? Is it radical based? Or does the $$\ce{MnO4-}$$ ion react with tetracene in a similar manner as alkenes are hydroxylated to diols?

Do I have to consider the inherent aromaticity of tetracene to deduce which "double bond" (because there's no "true" double bond) the $$\ce{MnO4-}$$ species reacts with?

• My money is on either phthalic acid or the 1,2,4,5-tetracarboxylic acid. – Jan Jun 5 '16 at 17:25
• I'm guessing quinone will be at least intermediate. – Mithoron Jun 5 '16 at 18:25
• @Jan Sounds reasonable, since naphthalene is oxidized to phthalic acid under these conditions. – Klaus-Dieter Warzecha Jun 6 '16 at 8:33