Fantasma4500
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Posts: 1677
Registered: 12-12-2012
Location: Dysrope (aka europe)
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amine to nitro- chromium complex?
so- im trying to accomplish amine into nitro compounds
https://gyazo.com/d65ac97d85c49fdf8984f3010fe48f17
im reading that it can be done with just manganate- basified KMnO4? but i have a bunch of CrO3 so i went ahead with H2CrO4 knowing well that it turns
ethanol into aldehyde same second
so i add in an amount, the red H2CrO4 turns yellowish very fast and the smell of amine eventually disappears - i try to light the contents of the
flask to get a nitroflame- nothing.
i cool it down a bit and plan to try to extract it with ethyl formate, but add some NaOH prior this to turn the excess H2CrO4 into NaCrO4 so it doesnt
just oxidize my poor solvent
now the smell of amine re-appears again.
turns out i might have a complex!! does this mean H2CrO4 is completely useless in this reaction? i did see KHSO5+acetone listed as useful for this,
and again- manganate (which is very doable by MnO2 + NaOH) does anyone by chance have experience with these complexes?
http://organicreactions.org/index.php/Oxidation_with_chromium(VI)-amine_complexes#:~:text=Oxidation%20with%20chromium(VI)%2Damine%20complexes%20involv
es%20the%20conversion,oxide%2Damine%20adducts%20and%20salts.
i did heat the mixture for a bit but barely at 60*C because i didnt wanna lose any material
i came across material that mentioned oxidizing amino acids prior decarboxylation- but now i worry that chromic acid would also complex with this?
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clearly_not_atara
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In the oxidation of amines, there is competing hydrolysis to the ketone, Beckmann rearrangement, C-oxidation at ipso and alpha positions, and
dimerization. As such, simply adding a random oxidizer to an amine is likely to yield a "complex mixture".
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Fantasma4500
International Hazard
Posts: 1677
Registered: 12-12-2012
Location: Dysrope (aka europe)
Member Is Offline
Mood: dangerously practical
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so- i want to add in an excess of chromic acid to try to push it towards oxidation? the amine was obviously unreacted, so im not sure if its forming a
ketone because that should be harder to reverse than just adding a tiny amount of NaOH
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