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The Clemmensen reduction is a chemical reaction described as a reduction of ketones (or aldehydes) to alkanes using zinc amalgam and hydrochloric acid.123 This reaction is named after Erik Christian Clemmensen, a Danish chemist.4
Several reviews have been published.5678
The Clemmensen reduction is particularly effective at reducing aryl-alkyl ketones.910 With aliphatic or acyclic ketones, zinc metal reduction is much more effective.11
The substrate must be stable in the strongly acidic conditions of the Clemmensen reduction. Acid sensitive substrates should be reacted in the Wolff-Kishner reduction, which utilizes strongly basic conditions. As a result of Clemmensen Reduction, the carbon of the carbonyl group involved is converted from sp2 hybridisation to sp3 hybridisation. The oxygen atom is lost in the form of one molecule of water.
References
- ^ Clemmensen, E. Ber. 1913, 46, 1837.
- ^ Clemmensen, E. Ber. 1914, 47, 51.
- ^ Clemmensen, E. Ber. 1914, 47, 681.
- ^ Biographies of Chemists, accessed 6 Feb 2007.
- ^ Martin, E. L. Org. React. 1942, 1, 155. (Review)
- ^ Buchanan, J. G. St. C.; Woodgate, P. D. Quart. Rev. 1969, 23, 522. (Review)
- ^ Vedejs, E. Org. React. 1975, 22, 401. (Review)
- ^ Yamamura, S.; Nishiyama, S. Comp. Org. Syn. 1991, 8, 309-313.(Review)
- ^ Organic Syntheses, γ-Phenylbutyric acid, Coll. Vol. 2, p.499 (1943); Vol. 15, p.64 (1935).
- ^ Organic Syntheses, Creosol, Coll. Vol. 4, p.203 (1963); Vol. 33, p.17 (1953).
- ^ Organic Syntheses, Modified Clemmensen Reduction: Cholestane, Coll. Vol. 6, p.289 (1988); Vol. 53, p.86 (1973).
See also
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