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Topic: oxymercuration adds h and oh in a what configuration? syn or anti?  (Read 15560 times)

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Offline miaou5

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oxymercuration adds h and oh in a what configuration? syn or anti?
« on: May 03, 2012, 02:57:38 AM »
i know that hydroboration adds h and oh to an alkene in a syn configuration, but how about oxymercuration? is it syn or anti, or racemic? thanks!
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Offline discodermolide

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Re: oxymercuration adds h and oh in a what configuration? syn or anti?
« Reply #1 on: May 03, 2012, 05:30:27 AM »
Quote from: miaou5 on May 03, 2012, 02:57:38 AM
i know that hydroboration adds h and oh to an alkene in a syn configuration, but how about oxymercuration? is it syn or anti, or racemic? thanks!


It gives a Markovnikov addition. It must be racemic and as you are adding OH and H how can it be syn or anti?
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Offline orgopete

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Re: oxymercuration adds h and oh in a what configuration? syn or anti?
« Reply #2 on: May 03, 2012, 09:09:50 AM »
The addition is an anti-addition. The product is a mercury alcohol. The demecuration reaction has been reported to be a radical reaction. Therefore, the relative stereochemistry created in opening the mecrurinium ion is lost during the reduction step. So, it is the last step that loses the syn/anti distinction, unlike hydroboration/oxidation.
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Offline miaou5

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Re: oxymercuration adds h and oh in a what configuration? syn or anti?
« Reply #3 on: May 06, 2012, 01:03:27 PM »
thank you so much pete! that makes sense. (:
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