Azoxy compounds

[2] Such reactions are proposed to proceed via the intermediacy of the nitroso compounds and hydroxylamines, e.g. phenylhydroxylamine and nitrosobenzene (Ph = phenyl, C6H5):[3]: 445

[4] Trans-azoxydibenzene's resonance form with a negative formal charge on oxygen (–N=N+(O−)–) corresponds to a theoretical 6‑D dipole moment.

However, the observed moment is only 4.7 D, suggesting a substantial resonance contribution in which the other nitrogen bears negative charge (–N−–N+(=O)–).

[5]: 42 Under ultraviolet light transazobenzene compounds isomerize to their cis isomers, analogous to azobenzene.

Azoxyarenes undergo the Wallach rearrangement to para-azophenols; primary and secondary azoxyaliphates tautomerize to a hydrazamide.

Single-electron reductants give a deep-blue radical anion, which dimerizes in aqueous solution to the corresponding azo compound and hydrogen peroxide.

Strong reducing agents such as lithium aluminum hydride also hydrogenolyze electronegative ortho or para arene substituents, but catalytic hydrogenation selects out the azoxy link.

The structure of the azoxy functional group, where R is a substituent .
Structure of azoxybenzene as determined by X-ray crystallography . [ 4 ]