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Topic: The conversion of a Malonate to an Acrylate  (Read 3892 times)

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Offline lutesium

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The conversion of a Malonate to an Acrylate
« on: February 26, 2010, 11:19:40 AM »
Is there a name reaction for this conversion???
If the answer is no can someone explain the mechanism please???

 

Offline Arctic-Nation

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Re: The conversion of a Malonate to an Acrylate
« Reply #1 on: February 26, 2010, 12:45:42 PM »
This probably is a two-step reaction. First, the malonic acid is decarboxylated, followed by a condensation with formaldehyde. You can easily find the mechanism for both.

Offline Smrt guy

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Re: The conversion of a Malonate to an Acrylate
« Reply #2 on: February 26, 2010, 09:54:13 PM »
Looks like a decarboxylation followed by a Mannich reaction

Offline lutesium

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Re: The conversion of a Malonate to an Acrylate
« Reply #3 on: February 27, 2010, 05:39:10 AM »
I knew that it was a decarboxylation but with these reagents how do they make a Mannich Reacton???
The main question in here is after decarboxylation with heat where can we apply the Mannich Reaction and where's the diEthyl Amine???

Offline Arctic-Nation

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Re: The conversion of a Malonate to an Acrylate
« Reply #4 on: February 27, 2010, 06:22:09 AM »
Ah, Mannich, I knew it had a name but I'm losing my touch.

Decarboxylation leads to the loss of only one carboxylate, so after that you have intermediate form known as an alpha-carboxylate dianion. This is a pretty basic compound (usually it is prepared by reacting a carboxylic acid with LDA or even stronger bases). A rapid equilibration will happen, but I think that the small amount present will react readily with the Mannich reagent, shifting the equilibrium. After that, another acid/base shift will lose the diethylamine and convert the whole thing to an exomethylene.

At least, that's my idea. I might be wrong.

Offline lutesium

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Re: The conversion of a Malonate to an Acrylate
« Reply #5 on: February 28, 2010, 05:36:19 AM »
I couldn't figure out what you tried to indicate!!! Can you draw a mechanism please???

Thanks

Lutesium...

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