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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.
The Gomberg–Bachmann reaction, named for the Russian-American chemist Moses Gomberg and the American chemist Werner Emmanuel Bachmann, is an aryl-aryl coupling reaction via a diazonium salt. [1] [2] [3] The arene compound (here benzene) is reacted with a diazonium salt in the presence of a base to provide the biaryl through an intermediate ...
Diazonium compounds or diazonium salts are a group of organic compounds sharing a common functional group [R−N + ≡N]X − where R can be any organic group, such as an alkyl or an aryl, and X is an inorganic or organic anion, such as a halide. The parent compound where R is hydrogen, is diazenylium.
In one important reaction type, a main group organometallic compound of the type R-M (where R = organic group, M = main group centre metal atom) reacts with an organic halide of the type R'-X with formation of a new carbon-carbon bond in the product R-R'. The most common type of coupling reaction is the cross coupling reaction. [1] [2] [3]
N-(1-Naphthyl)ethylenediamine dihydrochloride is widely used in the quantitative analysis of nitrate and nitrite in water samples by colorimetry.It readily undergoes a diazonium coupling reaction in the presence of nitrite to give a strongly colored azo compound.
Alizarine Yellow R is a yellow colored azo dye made by the diazo coupling reaction. It is usually commercially available as a sodium salt. It is usually commercially available as a sodium salt. In its pure form, it is a rust-colored solid. [ 2 ]
More recently, trifluoromethylation of diazonium salts has been developed and is referred to as a 'Sandmeyer-type' reaction. Diazonium salts also react with boronates, iodide, thiols, water, hypophosphorous acid and others, [6] and fluorination can be carried out using tetrafluoroborate anions (Balz–Schiemann reaction). However, since these ...
The Meerwein arylation is an organic reaction involving the addition of an aryl diazonium salt (ArN 2 X) to an electron-poor alkene usually supported by a metal salt. [1] The reaction product is an alkylated arene compound. The reaction is named after Hans Meerwein, one of its inventors who first published it in 1939. Meerwein arylation