Azoxy compounds are a group of chemical compounds sharing a common functional group with the general structure RN=N+(O−)R. They are considered N-oxides of azo compounds. Azoxy compounds are 1,3-dipoles. They undergo 1,3 dipolar cycloaddition with double bonds.
Most azoxy-containing compounds have aryl substituents. They are typically prepared by reduction of nitrocompounds, such as the reduction of nitrobenzene with arsenous oxide. Such reactions are proposed to proceed via the intermediacy of the hydroxylamine and nitroso compounds, e.g. phenylhydroxylamine and nitrosobenzene:
- PhNHOH + PhNO → PhN(O)NPh + H2O
- IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "azoxy compounds".
- H. E. Bigelow and Albert Palmer "Azoybenzene" Org. Synth. 1931, 11, 16. doi:10.15227/orgsyn.011.0016
- Guideline On The Limits Of Genotoxic Impurities "Archived copy" (PDF). Archived from the original (PDF) on 2006-09-04. Retrieved 2007-07-11.