Maintenance Notice (5:15 AM - 4:55 PM May 24, 2025): This website is scheduled to be unavailable due to maintenance. We appreciate your patience and understanding.
Published TCIMAIL newest issue No.197
Maximum quantity allowed is 999
Bitte wählen Sie die Menge aus.
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:
-
- 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:
-
- The Mechanism of the Wolff-Kishner Reduction, Elimination, and Isomerization
