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Topic: Converting 1,4-dimethoxybenzene into quinone  (Read 3822 times)

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Offline g_orbital

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Converting 1,4-dimethoxybenzene into quinone
« on: May 22, 2006, 12:58:17 PM »
I have found a reaction which converts 1,4-dimethoxybenzene derivative into the benzoquinone derivative, by two different synthetic methods: The one uses CAN (ammonium cerium nitrate), CH3CN-H2O. The other one makes use of AgO + HNO3 in dioxane.

What's the mechanism of this conversion in each method?

Thank you very much indeed!

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Re: Converting 1,4-dimethoxybenzene into quinone
« Reply #1 on: May 22, 2006, 04:38:56 PM »
Where did you come across this?  A guy in my lab recently finished a synthesis of that molecule as well.

As to your question, both of those reagents likely function through sequential one-electron oxidations wherein an electron is  "pulled out" of the electron rich aromatic system in the substrate and onto your oxidizing agent.  Eventually the methyl groups fall off, probably via SN2 attack by water.

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