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Topic: Allylic oxidation question  (Read 1444 times)

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Offline AlphaScent

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Allylic oxidation question
« on: June 13, 2013, 03:59:03 PM »
So I have a question,

Can you selectively oxidize a terminal alkene that is conjugated to a internal alkene? To yield a alcohol?  I know selenium dioxide works, but the aldehyde is a byproduct and then you reduce.  Not that bad, just wondering if there is a way to cleanly go to the primary, allylic alcohol?

Cheers!!

KCCO!
If you're not part of the solution, then you're part of the precipitate

Offline camptzak

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Re: Allylic oxidation question
« Reply #1 on: June 13, 2013, 07:20:48 PM »
So I have a question,

Can you selectively oxidize a terminal alkene that is conjugated to a internal alkene? To yield a alcohol?  I know selenium dioxide works, but the aldehyde is a byproduct and then you reduce.  Not that bad, just wondering if there is a way to cleanly go to the primary, allylic alcohol?

Cheers!!

KCCO!

Can you use selenium dioxide on a terminal alkene conjugated to an internal alkene? the mechanism shown on this page: http://en.wikipedia.org/wiki/Organoselenium_chemistry
shows something different
could you show me with structure diagrams?
"Chance favors the prepared mind"
-Louis Pasteur

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