Oxidation to nitriles...

The mechanism is that the NBS brominates the amine what will immediately form an imine while a HBr eliminates from with a hydrogen from the alpha position, this will cause the decarboxylation of the COOH, what is followed by another bromiation what will go on the imine what will release a HBr and the nitrile is formed woala.

Same works at the TCCA method.


But, nitriles are usually formed by much easier reactions:
subtitution (halogen and nitrile)
dehydration of an amide with P2O5, SOCl2, POCl3 ect. (just made some trifluroacetonitrile from trifluroacetamide and P2O5, it is an awesome rxn )
from amides with grignards
from aldehydes with hydroxylamine

Quote: Originally posted by chrisbob44

So recently I ran into these articles, and was wondering if someone could elucidate the mechanism at work here... http://www.erowid.org/archive/rhodium/pdf/aminoacid.decarbox... http://www.organic-chemistry.org/abstracts/lit2/979.shtm I ran into the organic-chemistry article first, and was kinda skeptical (the article came out of Iran...), but then I ran into this erowid rhodium archive article, and my interest was piqued... I was imagining something that involved the amine being pushed to a higher oxidation state, but quite frankly I'm pulling that out of my ass, so any help would be appreciated.

Don't have glassware mate As a first year chem student, I'm damn broke, but when I do slop some funds together, I promise this'll be on the top of my beaker list.

Quote: Originally posted by kristofvagyok

The mechanism is that the NBS brominates the amine what will immediately form an imine while a HBr eliminates from with a hydrogen from the alpha position, this will cause the decarboxylation of the COOH, what is followed by another bromiation what will go on the imine what will release a HBr and the nitrile is formed woala. Same works at the TCCA method.