Chemistry Organic Building Blocks Azoes
Azo compounds refer to a type of organic compound that contains the diazenyl functional group (R−N=N−R′), where the R and R′ groups may be aryl or alkyl.
According to IUPAC, azo compounds are described as derivatives of diazene (diimide), HN=NH, where both hydrogen atoms are replaced by hydrocarbyl groups. An example of this is azobenzene or diphenyldiazene, which can be represented as PhN=NPh.
Aryl azo compounds typically exist as stable, crystalline species. Azobenzene, which is the archetypal aromatic azo compound, predominantly exists as the trans isomer. However, it can be converted to the cis isomer upon illumination.
The synthesis of aromatic azo compounds can be achieved through azo coupling, which involves an electrophilic substitution reaction. In this process, an aryl diazonium cation is attacked by another aryl ring, particularly those containing electron-donating groups.
Aryl azo compounds are more commonly encountered than their aliphatic counterparts. Nonetheless, an alkyl azo compound of commercial significance is azobisisobutyronitrile (AIBN), extensively employed as an initiator in free-radical polymerizations and other radical-induced reactions.
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4,4-(1,2-Diazenediyl)bis[1,2-benzenedicarboxylic acid]
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(E)-4,4'-(Diazene-1,2-diyl)bis(2-methylbenzoic acid)
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1-((4-Methyl-2-nitrophenyl)diazenyl)naphthalen-2-ol
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Diazene-1,2-diylbis(piperidin-1-ylmethanone)
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1-((4-Nitrophenyl)diazenyl)naphthalen-2-ol
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4-((4-(Dimethylamino)phenyl)diazenyl)benzenesulfonic acid, sodium salt
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1-((4-Methyl-2-nitrophenyl)diazenyl)naphthalen-2-ol
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Diisopropyl diazene-1,2-dicarboxylate
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1-((4-Nitrophenyl)diazenyl)naphthalen-2-ol