chemistry Chemistry is the science, scientific study of the properties and behavior of matter. It is a natural science that covers the Chemical element, elements that make up matter to the chemical compound, compounds made of atoms, molecules and ions ...

, azoxy compounds are a group of

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

s sharing a common

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...

with the general structure . They are considered N-oxides of

azo compound Azo compounds are organic compounds bearing the functional group diazenyl (, in which R and R′ can be either aryl or alkyl groups). IUPAC defines azo compounds as: "Derivatives of diazene (diimide), , wherein both hydrogens are substituted ...

s. Azoxy compounds are 1,3-dipoles. They undergo 1,3-dipolar cycloaddition with double bonds.

Preparation

Most azoxy-containing compounds have

aryl In organic chemistry, an aryl is any functional group or substituent derived from an aromatic ring, usually an aromatic hydrocarbon, such as phenyl and naphthyl. "Aryl" is used for the sake of abbreviation or generalization, and "Ar" is used as ...

substituents. They are typically prepared by reduction of nitrocompounds, such as the reduction of

nitrobenzene Nitrobenzene is an organic compound with the chemical formula C6H5 NO2. It is a water-insoluble pale yellow oil with an almond-like odor. It freezes to give greenish-yellow crystals. It is produced on a large scale from benzene as a precursor t ...

with arsenous oxide to

azoxybenzene Azoxybenzene is organic compound with the formula C6H5N(O)NC6H5. It is a yellow, low-melting solid. The molecule has a planar C2N2O core. The N-N and N-O bond lengths are nearly the same at 1.23 Å. Preparation It can be prepared by partial re ...

. Such reactions are proposed to proceed via the intermediacy of the hydroxylamine and nitroso compounds, e.g.

phenylhydroxylamine Phenylhydroxylamine is the organic compound with the formula C6H5NHOH. It is an intermediate in the redox-related pair C6H5NH2 and C6H5NO. Phenylhydroxylamine should not be confused with its isomer α-phenylhydroxylamine or ''O''-phenylhydroxyl ...

and

nitrosobenzene Nitrosobenzene is the organic compound with the chemical formula, formula C6H5NO. It is one of the prototypical organic nitroso compounds. Characteristic of its functional group, it is a dark green species that exists in equilibrium with its pale ...

(Ph =

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...

, ): :PhNHOH + PhNO -> PhN(O)NPh + H2O

Safety

Alkyl azoxy compounds, e.g.

azoxymethane Azoxymethane (AOM) is a carcinogenic and neurotoxic chemical compound used in biological research. It is the oxide of azomethane and is particularly effective for the induction of a colon carcinoma Carcinoma is a malignancy that develops from ...

are suspected to be genotoxic.Guideline On The Limits Of Genotoxic Impurities

References

{{Authority control Functional groups Azo compounds