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Topic: Please tell me the mechanism of this reaction?  (Read 1883 times)

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Offline liuj975

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Please tell me the mechanism of this reaction?
« on: September 13, 2012, 08:19:52 AM »
Could any nice guy tell me the mechanism of this reaction (attachment)?

Offline Doc Oc

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Re: Please tell me the mechanism of this reaction?
« Reply #1 on: September 13, 2012, 08:45:20 AM »
Take a look at this paper.  Although they use IBX and not BAIB, the concept remains the same.

http://pubs.acs.org/doi/abs/10.1021/ja012127%2B?journalCode=jacsat

Offline orgopete

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Re: Please tell me the mechanism of this reaction?
« Reply #2 on: September 13, 2012, 02:43:30 PM »
I expect this is written erroneously. I think it probably is 1) PhI(OAc)2 and 2) Zn. Otherwise I might think the zinc would reduce the iodonium salt. I don't think that is the reaction.

I think this is a two step process. First oxidation of the sulfur and reduction of the (oxidized) ketene thioacetal. Can you make a suggestion if that is the process?

Even if I am wrong (which could be), it may still be easier to understand the reaction if you drew it as a two step process.
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