Do amides from primary or secondary amines ever oxidize to a double-bond on the nitrogen? For example, like from an $\mathrm{R \bbox[yellow]{\color{red}{-}}(NH)-(C=O)-R'}$ to an $\mathrm{ R \bbox[yellow]{\color{red}{=}}N-(C=O)-R'}$?

Seems like a favorable product, given the creation of that conjugated pi-bonded system! But, I can't seem to find any references to such a reaction -- would it perhaps require some kind of elimination groups on the amine as well?

  • $\begingroup$ The metabolism of acetaminophen to NAPQI looks like that, although it does involve the formation of the quinone as well. $\endgroup$ – ralk912 Mar 17 '18 at 2:27

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