Aryl-NNO-azoxy-?-nitroalkanes

Abstract

Two methods of synthesis of aryl-NNO-azoxy-α-nitroalkanes bearing either one or two reactive hydrogen atoms α to the azoxy and nitro groups are described. These methods involve protection of the latter by easily removable groupings, those used being acetoxy-methyl and acetal fragments. The regiochemical nature of the diazene oxide groupings in aryl-NNO-azoxy-α-nitroalkanes obtained by oxidation of the appropriate diazenes has been established by heteronuclear NMR and x-ray structural examination. Some of the chemical properties of these diazene oxides have been examined.