LabRatNW
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Oxidation of Nitriles to Nitro groups
Has anyone played around with this idea before?
The idea is, generating an easy supply of Nitroalkanes or other nitro containing groups for fuel or synthetic material.
ACN + Oxidizer -> EtNO2 (Not necessarily functional, but the idea is there)
[Edited on 1-25-2019 by LabRatNW]
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clearly_not_atara
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It doesn't really work. The nitrile oxide is produced and it dimerizes to a furoxan.
You can make nitro compounds from oximes by a complex method due to Corey, but it works by adding chlorines to the alpha carbon so that it won't get
oxidized. Then the chlorines are reduced to leave the nitro compound.
And even if it did work acetonitrile isn't that easy to come by, or at least I don't see anyone using it, so I assume it must not be.
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LabRatNW
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Acetonitrile is easy as hell to get.
I don't know how it would dimerize to furoxan, That doesn't even make sense. How would you suddenly end up with another nitrogen on the methyl
carbon?
[Edited on 1-25-2019 by LabRatNW]
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CuReUS
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http://www.publishchemidea.com/direct-conversion-of-nitriles...
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clearly_not_atara
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Two equivalents of acetonitrile oxide dimerize to 4,5-dimethylfuroxan.
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LabRatNW
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Is there a published mechanism for that?
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clearly_not_atara
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https://pubs.acs.org/doi/abs/10.1021/ja037325a
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zed
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Oxidations are quirky. Hard to stop 'em on a dime.
Acetonitrile can be reduced to Ethylamine.
Which in turn, can be oxidized to Nitroethane, via Oxone-Acetone?
But, it is a fussy business involving lots of solvent.
Alas, the industrial techniques utilized by big chem, work very well at producing large quantities of inexpensive nitroalkanes.
Nitroalkanes, that most of us have difficulty accessing, and few good alternatives for synthesizing.
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