Clemmensen reduction

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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.[1][2][3]

The Clemmensen reduction

Several reviews have been published.[4][5][6][7]

The Clemmensen reduction is particularly effective at reducing aryl-alkyl ketones.[8][9] With aliphatic or acyclic ketones, zinc metal reduction is much more effective.[10]

The substrate must be stable in the strongly acidic conditions of the Clemmensen reduction. Acid sensitive substrates should use the Wolff-Kishner reduction, which utilizes strongly basic conditions.

[edit] References

  1. ↑  Clemmensen, E. Ber. 1913, 46, 1837.
  2. ↑  Clemmensen, E. Ber. 1914, 47, 51.
  3. ↑  Clemmensen, E. Ber. 1914, 47, 681.
  4. ↑  Martin, E. L. Org. React. 1942, 1, 155. (Review)
  5. ↑  Buchanan, J. G. St. C.; Woodgate, P. D. Quart. Rev. 1969, 23, 522. (Review)
  6. ↑  Vedejs, E. Org. React. 1975, 22, 401. (Review)
  7. ↑  Yamamura, S.; Nishiyama, S. Comp. Org. Syn. 1991, 8, 309-313. (Review)
  8. ↑  Organic Syntheses, Coll. Vol. 2, p.499 (1943); Vol. 15, p.64 (1935). (Article)
  9. ↑  Organic Syntheses, Coll. Vol. 4, p.203 (1963); Vol. 33, p.17 (1953). (Article)
  10. ↑  Organic Syntheses, Coll. Vol. 6, p.289 (1988); Vol. 53, p.86 (1973). (Article)

[edit] See also

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