Sciencemadness Discussion Board - Is it an enolate?


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ChemistryGhost

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posted on 1-9-2012 at 19:56

Is it an enolate?

I want to know if the product from the Fe3+ catalized oxidation of sesamol is an enolate. Is it an enolate? It's reacting with itself. Is it an aldol condensation?

http://www.sciencedirect.com/science/article/pii/S0040403909...

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triplepoint

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posted on 1-9-2012 at 20:24

I believe not. I think that an enolate requires a double bond between O and C. I believe that an aldol condensation also requires that you begin with a double bond between O and C.

I am sure that you will receive more detailed answers form those more knowledgeable than I.

Siggebo

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posted on 1-9-2012 at 21:54

The first reaction step, you mean?

The Ar-OH ring you have there is actually an enol (ph-enol, eh?

) and it's equilibrium is far to the enol side. The first step seems to be a conversion into the keto tautomer (with Fe3+ as acid catalyst) and then you have a radical reaction, not an aldol-type reaction. You can tell by the "fish-hook" arrows, with one hook denoting one electron. Compare the two-hook ordinary curly arrows indicating electron pair movement.

And do correct me if I'm wrong. It happens all the time.