Silver carbonate, a convenient reagent for preparing <i>C</i>‐nitroso compounds from hydroxylamines

Maassen, J. A.; Boer, Th. J. de

doi:10.1002/recl.19710900405

Cited by 24 publications

(1 citation statement)

References 4 publications

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“…The reaction of nitroso derivatives 21 with aniline 22 leads to the azobenzenes 23 with good overall yields. Other oxidation agents like ferric chloride, 27 Caro's acid (H 2 SO 5 ), 28 sodium or potassium dichromate and sulfuric acid, 29 m-chloroperbenzoic acid, 31 potassium permanganate, 32 ferric chloride, 33 diethyl azodicarboxylate, 34 iodine/NaI/NaOAc, 35 silver carbonate, 36 (diacetoxyiodo)benzene, 37 2,3-dichloro-5,6dicyanobenzoquinone (DDQ) 38 and peroxyformic acid 39 have been used to generate the nitroso aromatic derivative.…”

Section: Mills Reactionmentioning

confidence: 99%

Synthesis of azobenzenes: the coloured pieces of molecular materials

2011

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Azobenzenes are ubiquitous motifs very important in many areas of science. Azo compounds display crucial properties for important applications, mainly for the chemical industry. Because of their discovery, the main application of aromatic azo compounds has been their use as dyes. These compounds are excellent candidates to function as molecular switches because of their efficient cis-trans isomerization in the presence of appropriate radiation. The classical methods for the synthesis of azo compounds are the azo coupling reaction (coupling of diazonium salts with activated aromatic compounds), the Mills reaction (reaction between aromatic nitroso derivatives and anilines) and the Wallach reaction (transformation of azoxybenzenes into 4-hydroxy substituted azoderivatives in acid media). More recently, other preparative methods have been reported. This critical review covers the various synthetic methods reported on azo compounds with special emphasis on the more recent ones and their mechanistic aspects (170 references).

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