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Sandmeyer Reaction

Sandmeyer reaction   Named Reactions in Organic Synthesis

Reaction category:
Radical reactions!

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In 1884, Swiss chemist Traugott Sandmeyer attempted to synthesize phenylacetylene from benzenediazonium chloride and copper(I) acetylide. However, the main product he isolated was chlorobenzene and no trace of the desired product was found. On careful examination of the reaction it was discovered that copper(I) chloride was formed in situ, which catalysed the replacement of the diazonium group with a chlorine atom. Following this discovery the substitution of aryldiazonium salts with halides or pseudo halides became known as the Sandmeyer reaction.

The required aryldiazonium halides are generally prepared from the corresponding arylamines via diazotisation using sodium nitrite and aqueous hydrochloric acid or alkyl nitrites such as tert-butyl nitrite under anhydrous conditions. These aryldiazonium compounds are prepared and reacted in situ with copper(I) chloride, bromide or cyanide to obtain the corresponding aryl halide or nitrile.

The Sandmeyer reaction has been used in many successful synthesis campaigns including the preparation of the anti-psychotic drug flupentixol and neoamphimedine, a compound that has anti-cancer properties.


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Pericyclic and photochemical reactions NEW!

Electrophilic aromatic substitution

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Heterocycle formation

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Oxidation

Reactions involving carbonyl compounds

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Some relevant Alfa Aesar products for the Sandmeyer reaction:

Sodium nitrite, 98%
Sodium nitrite, ACS, 97% min
Copper(I) chloride, 97%
Copper(I) chloride, 99% (metals basis)
Copper(I) chloride, 99.999% (metals basis)
Copper(I) bromide, 98%
Copper(I) cyanide
Potassium iodide, 99%
Potassium iodide, ACS, 99.0% min
Potassium iodide, 99.9% (metals basis)


We have many aryl amines in our portfolio.

 

 

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