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Author: Subject: Oxidation of phenethylamine to (2-nitroethyl)benzene
Nicodem
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[*] posted on 24-7-2008 at 01:39


Excellent find, thanks Klute!
I don't know what practical use could such a reaction have, but this is the first paper I saw that describes good to excellent yields in N-oxidation of R-CH2-NH2 type of amines to nitro compounds.
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sonogashira
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[*] posted on 24-7-2008 at 01:58


The reference was actually posted by quantum_dom in the very first post of this thread, though i guess he didn't have access to the paper.

Nicodem: "this is the first paper I saw that describes good to excellent yields in N-oxidation of R-CH2-NH2 type of amines to nitro compounds."

Here's another one (also given in the first post! The others concern oxidation of aromatic amines) using isomers of butylamine:

Attachment: Nitroalkanes from Amines with DMDO.pdf (119kB)
This file has been downloaded 897 times

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Quantum_Dom
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[*] posted on 26-7-2008 at 16:35


Many thanks sonogashira !!! :D

Finally I can take a peek at those papers :)

Cheers.
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Ephoton
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[*] posted on 27-7-2008 at 02:21


do you think this reaction will work for ethylamine.

it states butyl amine as the lowest alphatic amine in it examples.

would nitro ethane azeotrope with the acetone in the dioxane solution.




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secunder2
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[*] posted on 31-7-2008 at 10:16


Can anyone help me if i have a serious problem?
The question is:

that can the phenyl-2-nitrostyrene change to phenyl-2-nitropropene with formaldehyde and if it reacts what kind of catalizator is needed or not needed to complete the reaction?

thanks everybody

secunder
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Klute
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[*] posted on 31-7-2008 at 15:41


That's not possible in a one step reaction, and I highly doubt it's possible.

Addition of formaldehyde to the double bond would form 2-nitro-1-phenylpropan-3-ol ("b-(hydromethy)phenyl-b-nitroethane") . You would have to dehydrate this to obtain the alcene, which would surely partially rearrange to the nitropropene, but both steps would surely give alot of byproducts, polycondensations and other tar-forming reactions.




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secunder2
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[*] posted on 1-8-2008 at 01:39


First of all thanks again Klute

Then how can I convert my phenyl-2-nitrostyrene to phenyl-2-nitropropene?
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stoichiometric_steve
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[*] posted on 1-8-2008 at 04:28


Quote:
Originally posted by secunder2
First of all thanks again Klute

Then how can I convert my phenyl-2-nitrostyrene to phenyl-2-nitropropene?


yeast

think about other ways to make amphetamine.




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arsenic
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[*] posted on 3-8-2008 at 15:37


The nitro group in organic synthesis

read the second chapter,

[Edited on by arsenic]
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Filemon
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[*] posted on 6-8-2008 at 15:31


What does it produce a primary amine with H2O2? a nitroso?

[Edited on 6-8-2008 by Filemon]
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Klute
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[*] posted on 6-8-2008 at 15:39


An oxide, presumally. hindered secondary amines can form stable nitrosyl radicals (2,2,6,6-tetramethylpiperidine, diisopropylamine, etc..)



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Filemon
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[*] posted on 8-8-2008 at 07:48


Him little that I have found H2O2 it oxidizes a secondary amine to hydroxilamine. It compares the activity of H2O2 with a peracid.



[Edited on 8-8-2008 by Filemon]
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Maja
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[*] posted on 10-9-2008 at 10:27


What are the conditions when condensing formaldehyde with phenylnitroethane ? For catalyst using some amine or base, but what if formaldehyde is in water solution 40%? What solvent should I use ?

[Edited on 10-9-2008 by Maja]
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