Science of Synthesis

Li, W-R., Science of Synthesis, (2005) 21, 179.

Acyl nitroso compounds are not only used to prepare amides, but also have a wide range of applications as N—O heterodienophiles in the total syntheses of nitrogen-containing natural products.[‌1‌] The oxidation of readily available N-hydroxy amides (hydroxamic acids) in the presence of amines affords the corresponding amides, e.g. ‌2‌, via acyl nitroso compounds, e.g. ‌1‌ (‌Scheme 1‌).[‌2‌] Oxidations of a variety of hydroxamic acids in the presence of the same amine afford similar yields of the corresponding amide products. The use of nonhindered primary amines gives the highest yields of amides, and the yield decreases with increasing steric size.

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