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Conversion of N-Aromatic Amides to O-Aromatic Esters

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N-Aromatic secondary amines can be transformed into O-Aromatic esters in high yield via nitrosoamide intermediates which thermally rearrange (Glatzhofer D T et al, Org Lett, 2002, 4, 2349). By in situ formation of the amide, a telescoped reaction can occur as shown below.

Conversion of N-Aromatic Amides to O-Aromatic Esters