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In organic chemistry, an azo coupling is an reaction between a diazonium compound (R−N≡N +) and another aromatic compound that produces an azo compound (R−N=N−R’).In this electrophilic aromatic substitution reaction, the aryldiazonium cation is the electrophile, and the activated carbon (usually from an arene, which is called coupling agent), serves as a nucleophile.
Azo compounds are organic compounds bearing the functional group diazenyl (R−N=N−R′, in which R and R′ can be either aryl or alkyl groups).. IUPAC defines azo compounds as: "Derivatives of diazene (diimide), HN=NH, wherein both hydrogens are substituted by hydrocarbyl groups, e.g. PhN=NPh azobenzene or diphenyldiazene.", where Ph stands for phenyl group. [1]
2,2'-Azobis(2-amidinopropane) dihydrochloride (abbreviated AAPH or AMPA) is a chemical compound used to study the chemistry of the oxidation of drugs. [1]It is a free radical-generating azo compound.
Azobenzene is a photoswitchable chemical compound composed of two phenyl rings linked by a N=N double bond.It is the simplest example of an aryl azo compound.The term 'azobenzene' or simply 'azo' is often used to refer to a wide class of similar compounds.
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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.
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