Sciencemadness Discussion Board

Oxidation of amine to nitro in HMTD

Hunterman2244 - 24-7-2018 at 19:00

Is it possible to oxidize the amines in HMTD to nitro groups? Maybe via NaOCl?

Sigmatropic - 24-7-2018 at 21:09

They are tertiary amines, only primary amines can be oxidized to nitro groups. Perhaps the N-oxide can be made. But given that it is a hemiaminal ether I doubt it will be stable enough to isolate.

[Edited on 25-7-2018 by Sigmatropic]

Hunterman2244 - 26-7-2018 at 13:13

Quote: Originally posted by Sigmatropic  
They are tertiary amines, only primary amines can be oxidized to nitro groups. Perhaps the N-oxide can be made. But given that it is a hemiaminal ether I doubt it will be stable enough to isolate.

[Edited on 25-7-2018 by Sigmatropic]

Thanks, I saw something on primary amines, but wasn't sure.