Azoxy compounds

The structure of the azoxy functional group, where R is a substituent.

Azoxybenzene - An example azoxy compound.

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.

Preparation

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

Safety

Alkyl azoxy compounds, e.g. azoxymethane are suspected to be genotoxic.