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Topic: Periodate cleavage mechanism  (Read 5318 times)

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Offline wonka_vision

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Periodate cleavage mechanism
« on: September 28, 2010, 08:12:30 PM »
Hi everyone,
I'm interested to know how the intermediate cyclic periodic ester is formed in the cleavage of 1,2 diols with sodium periodate.
Any ideas?

Thanks!
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Offline MissPhosgene

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Re: Periodate cleavage mechanism
« Reply #1 on: November 21, 2010, 01:20:35 AM »
You can do that reaction using chloroform and say. bicarb solution as solvents.

You make water, but not by losing H2O from the glycol upon formation of the cyclic intermediate. Can you make a guess? The reaction to make the intermediate is not concerted.
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Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.
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