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 NO2to the carbon atom of the carbon-nitrogen double bond. © 2003 Elsevier Ltd. All rights reserved.
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