What is the role of solvent oxidation in the reaction of arylamines with SeO₂?

Label:chem

Topic
The study observed that solvent oxidation played a significant role in the reaction of arylamines with SeO₂ in acetonitrile. This pathway led to the formation of oxamides.

From: "Competing electrophilic substitution and oxidative polymerization of arylamines with selenium dioxide", Beilstein J. Org. Chem. 2024, 20, 1221–1235.
Answer
Solvent oxidation resulted in the formation of oxamides (e.g., compounds 3, 9, and 13) due to the interaction between the solvent (acetonitrile) and the acidic α-CH unit. The oxamides were characterized by FTIR, ¹H NMR, and mass spectrometry.
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