November 18, 2019, 03:12:42 PM
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Topic: What is the role of p-benzoquinone in Wacker oxidation?  (Read 237 times)

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Offline Cavve

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What is the role of p-benzoquinone in Wacker oxidation?
« on: April 08, 2019, 11:39:20 PM »
I was hoping that someone could help me, by clearing up my confusion by providing a somewhat detailed explanation of the role of p-benzoquinone, in terms of the mechanism it uses to regenerate Pd(0) to Pd(II). Typically, CuCl2 is used for this role, so why would one use this benzo, and how does it work? What other roles might p-benzoquinone play? I've heard as a source of oxygen??

Please and thanks,

Offline kriggy

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Re: What is the role of p-benzoquinone in Wacker oxidation?
« Reply #1 on: April 10, 2019, 01:22:10 AM »
I would say that benzoquinone is reduced to hydroquinone and it oxidizes the Pd back to Pd2+. Im not sure why they use this over the copper but I can see multiple reasons such as
a) enviromental concerns: its probably easier to disopose the quinone than the heavy metal co-catalyst
b) it just works better in the specific cases

dou you have literature example of this specific example?

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