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An aromatic (or heterocyclic) amine quickly reacts with a nitrite to form an aryl diazonium salt, which decomposes in the presence of copper(I) salts, such as copper(I) chloride, to form the desired aryl halide. The reaction is a radical-nucleophilic aromatic substitution.
The majority of variations of the Sandmeyer reactions consist of using various copper salts. For example, using cuprous cyanide produces benzonitriles. The use of tetrafluoroborate delivers the halide-substituted product, fluorobenzene. Substituting thiols or water for the copper salts generates thioethers or phenols, respectively.
Sandmeyer reactions with copper salts used in catalytic amounts are also known. One bromination protocol employs a 0.2 equivalent Cu(I)/Cu(II) mixture with additional amounts of the bidentate ligand phenanthroline and phase-transfer catalyst dibenzo-18-crown-6 :
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Sandmeyer_reaction". A list of authors is available in Wikipedia.|