The synthesis and reactions of hexahydrodioxotetrabenzoanthrylentriptycene
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The quinone (IV) adds to pentacene in the 6.13 and 5.14 positions forming the isomeric adducts (III) and (V).
The ketoalcohol (IX) is extremely unstable: its hydroxycyclohexenone grouping is oxidized by atmospheric oxygen to the corresponding hydroxycyclohexadienone.
On being heated to ∼ 140° (at a residual pressure of nitrogen of 5 mm or in solution in acetic anhydride) the ketoalcohol (XI) undergoes a rearrangement into the corresponding hydroquinone (in the latter case, with simultaneous acetylation).
All the compounds described have been obtained for the first time.
KeywordsOxygen Nitrogen Acetic Adduct Anhydride
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