ChemistryGhost
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Enols and Enamines?
Can it be possible to create (I don't know what it's called, let's call it ethylamine acetonate for now) by reacting acetone with ethylamine using
sulphuric acid in an enamine reaction?
Can reacting acetaldehyde using acid or base yield the enol of ethanol.
[Edited on 14-9-2012 by ChemistryGhost]
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vmelkon
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You seem to have an oxygen with 3 bonds there in your second picture. The first one is missing an oxygen.
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ChemistryGhost
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So in the first one, does it only work with secondary amines?
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zed
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Sulfuric acid is not required. Acetone and Ethylamine should react easily to form acetone ethyl-imine (plus H2O).
Although, an enamine form should be fairly unstable, I would assume that a small amount of enamine would always be present. Equilibrium.
The question is.....can this enamine form, be utilized in some useful way?
An old time acquaintance, once tried to utilize this hypothetically present enamine, in a Friedle-Crafts style alkylation.
His premise was, that he might be able to alkylate benzene with the enamine form of Acetone-Methylimine.
This would have provided him a quick and hysterically easy route to Methamphetamine.
Since civilization as we know it, still exists, I can only assume that he never succeeded.
[Edited on 15-9-2012 by zed]
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ChemistryGhost
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Quote: Originally posted by zed  | Sulfuric acid is not required. Acetone and Ethylamine should react easily to form acetone ethyl-imine (plus H2O).
Although, an enamine form should be fairly unstable, I would assume that a small amount of enamine would always be present. Equilibrium.
The question is.....can this enamine form, be utilized in some useful way?
An old time acquaintance, once tried to utilize this hypothetically present enamine, in a Friedle-Crafts style alkylation.
His premise was, that he might be able to alkylate benzene with the enamine form of Acetone-Methylimine.
This would have provided him a quick and hysterically easy route to Methamphetamine.
Since civilization as we know it, still exists, I can only assume that he never succeeded.
[Edited on 15-9-2012 by zed] |
Is the above synthesis possible? So I guess basically when it's with secondary amines, you get enamines and when it's with primary amines, you get
imines?
[Edited on 16-9-2012 by ChemistryGhost]
[Edited on 16-9-2012 by ChemistryGhost]
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ChemistryGhost
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For the second one, i found out the product is called Vinyl alcohol. It's unstable and readily converts to acetaldehyde.
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ChemistryGhost
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I found this.
http://www.sciencemag.org/content/337/6099/1203.abstract
So can vinyl alcohol be produced from acetaldehyde by exposure to sunlight?
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zed
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Such things relate to polymer chemistry. A topic I know nothing about.
Simple enols of the type you seem to be interested in, are pretty unstable. But, they can sometimes be obtained commercially in the form of
enol-esters.
Isopropenyl Acetate is an example. As is Vinyl Acetate.
[Edited on 21-9-2012 by zed]
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