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The reaction of the surface with a solution of diazonium salt in acetonitrile for 2 hours in the dark is a spontaneous process through a free radical mechanism: [42] Diazonium salt application silicon wafer. So far grafting of diazonium salts on metals has been accomplished on iron, cobalt, nickel, platinum, palladium, zinc, copper and gold ...
Azo printing exploits this reaction as well. In this case, the diazonium ion is degraded by light, leaving a latent image in undegraded diazonium salt which is made to react with a phenol, producing a colored image: the blueprint. [3] Prontosil, the first sulfa drug, was once produced by azo coupling. The azo compound is a prodrug that is ...
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 ...
The Sandmeyer reaction can also be used to convert aryl amines to phenols proceeding through the formation of an aryl diazonium salt. In the presence of copper catalyst, such as copper(I) oxide , and an excess of copper(II) nitrate , this reaction takes place readily at room temperature neutral water. [ 28 ]
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
To illustrate the mechanism, the Japp-Klingemann ester variation will be considered. The first step is the deprotonation of the β-keto-ester. The nucleophilic addition of the enolate anion 2 to the diazonium salt produces the azo compound 3. Intermediate 3 has been isolated in rare cases.
The reaction proceeds through a diazonium salt intermediate formed by displacement of the chloride with diazomethyl anion.. The Nierenstein reaction mechanism. If excess diazomethane is present during the reaction, it can act as a base, abstracting a hydrogen from the diazonium-salt intermediate.
This coupling can be carried out starting from anilines by formation of the diazonium salt followed by in situ Sonogashira coupling, where anilines are transformed into diazonium salt and furtherly converted into alkyne by coupling with phenylacetylene.