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Topic: Oxidation of sulfides to sulfoxides and sulfones.  (Read 6072 times)

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Offline ultima

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Oxidation of sulfides to sulfoxides and sulfones.
« on: April 18, 2011, 06:05:22 PM »
Hey all,

I've recently been trying to find some papers and literature on oxidation of sulfides to the corresponding sulfoxides/sulfones.
Typically, I've used reagents such as MCPBA (mainly for full oxidation to sulfone) and NaIO4 (mainly for selective oxidation to sulfoxides).

However Im trying to find mechanisms of these reactions. Does anyone know where i should start drawing arrows? Seems like it should be simple but its really confusing me!
Any help would be appreciated.
Thanks,

Offline orgopete

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Re: Oxidation of sulfides to sulfoxides and sulfones.
« Reply #1 on: April 23, 2011, 06:20:06 AM »
You should be able to write a mechanism that is the same as epoxide formation which I assume you can find. Just use the electrons from sulfur to initiate the reaction and to accept electrons from the oxygen and that should do it. Do the same with IO4-.
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Offline Kadabrium

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Re: Oxidation of sulfides to sulfoxides and sulfones.
« Reply #2 on: April 23, 2011, 06:36:08 AM »
peroxide might just transfer its oxygen atom to sulfur..IO4-maybe can form esterlike structures and then eliminate

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