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Wolff-Kishner Reduction
The Wolff-Kishner reaction is a classic, but basic method to convert ketones and aldehydes to methylene moieties via a hydrazone intermediate. Wolff and Kishner formed methylenes after isolating a semicarbazone and a hydrazone, respectively, and heating each. After their reports, Huang Minlon reported a modified method without isolating the hydrazone intermediate to afford the methylenes. In addition, some modifications have been reported since his report: Cram et al. reported a method using DMSO and potassium tert-butoxide at room temperature; Caglioti et al. reported a method using tosyl hydrazide and a hydride. The Wolff-Kishner reaction usually proceeds under basic conditions while the Clemmensen reduction proceeds under acidic conditions; therefore they can be applied complementarily.
- Reagents:
- Hydrazines, Base, DMSO, Lewis acids
- Reactants:
- Ketones, Aldehydes
- Products:
- Methylenes
- Scheme:
-
- Original literature:
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- N. Kishner, J. Russ. Phys. Chem. Soc. 1911, 43, 582.
- Chemischen Institut der Universität Jena: Methode zum Ersatz des Sauerstoffatoms der Ketone und Aldehyde durch Wasserstoff. [Erste Abhandlung.]
- A Simple Modification of the Wolff-Kishner Reduction
- Review literature:
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- The Mechanism of the Wolff-Kishner Reduction, Elimination, and Isomerization
