Sandmeyer reaction
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The Sandmeyer reaction is a chemical reaction used to synthesize aryl halides from aryl diazonium salts.
An aromatic (or heterocyclic) amine will quickly react with a nitrite to form an aryl diazonium salt. This diazonium salt will decompose in the presence of copper(I) salts (such as copper(I) chloride) to form the desired aryl halide.
Several improvements have been made to the standard procedures.
[edit] Variations
The majority of variations of the Sandmeyer reactions consist of using various copper salts. Using cuprous cyanide as the copper salt will produce benzonitriles.
The use of tetrafluoroborates which deliver the halide form for example fluorobenzene.
Substituting thiols or water for the copper salts will generate thioethers or phenols, respectively.
[edit] References
- ↑ Sandmeyer, T. Ber. 1884, 17, 1633.
- ↑ Sandmeyer, T. Ber. 1884, 17, 2650.
- ↑ Gattermann, L. Ber. 1890, 23, 1218.
- ↑ Kochi, J. K. J. Am. Chem. Soc. 1957, 79, 2942.
- ↑ Hodgson, H. H. Chem. Rev. 1947, 40, 251-277. (Review)
- ↑ Doyle, M. P. J. Org. Chem. 1977, 42, 2426.
- ↑ Suzuki, N. et al. Perkins Trans. I 1987, 645.
- ↑ Organic Syntheses, Coll. Vol. 1, p.514 (1941); Vol. 4, p.69 (1925). (Article)
- Organic Syntheses, Coll. Vol. 3, p.185 (1955); Vol. 24, p.22 (1944). (Article)
- Organic Syntheses, Coll. Vol. 4, p.160 (1963); Vol. 32, p.23 (1952). (Article)
