A novel reaction of ketone arylhydrazones with nitric oxide

The reaction of ketone arylhydrazone (1) with nitric oxide affords C1′-nitro azo-compounds (2) in good yields. Products were identified by NMR, IR, MS, and X-ray crystallography. The reaction is assumed to be most likely initiated by an electrophilic addition of NO2 to the carbon atom of the carbonnitrogen double bond.