Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Dea on July 30, 2007, 02:14:19 PM
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Hi all! :-)
I would appreciate if you told me where I could find something related to the mechanism of Michael addition of quinones with primary amines :-)
Thanks a lot! :-)
Dea
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I'm not sure if quinones are involved in Michael reactions. A Michael reaction involves a nucleophilic enolate ion reacting with an alpha,beta-unsaturated carbonyl compound. The most stable enolate ions are those derived from beta-keto esters or other 1,3-dicarbonyl compounds. Maybe the quinone could act as an alpha,beta-unsaturated carbonyl compound?
http://en.wikipedia.org/wiki/Quinone (http://en.wikipedia.org/wiki/Quinone)
http://en.wikipedia.org/wiki/Michael_reaction (http://en.wikipedia.org/wiki/Michael_reaction)
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A Michael addition is, strictly, the conjugate addition of a carbanion to an alpha-beta unsubstituted carbonyl compound. But many people use the name Michael addition to be almost synonymous with conjugate additions of any nucleophiles (including amines). The reaction you are thinking of is probably this:
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Thanks madscientist, Custos,
Yeah, I've been wondering why do they call the reaction "Michael" in the publication, but I thought there are some details I still don't know....:-)
Custos, that's what I was looking for. I still have a substituent on the 2-position on the quinone that gets replaced by the amine, I still get to figure that out :-)
Thanks, guys! :-)
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A Michael addition is, strictly, the conjugate addition of a carbanion to an alpha-beta unsubstituted carbonyl compound. But many people use the name Michael addition to be almost synonymous with conjugate additions of any nucleophiles (including amines). The reaction you are thinking of is probably this:
I think the Michael reaction is only with enolate nucleophiles as well.
It's more correct to call anything else a "conjugate addition."