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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?

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

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