Wolff Kishner Reaction – conversion of ketones/aldehydes to alkanes
Description: The Wolff-Kishner is a reaction for converting carbonyls (such as ketones and aldehydes) into alkanes.
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- Chemischen Institut der Universität Jena: Methode zum Ersatz des Sauerstoffatoms der Ketone und Aldehyde durch Wasserstoff. [Erste Abhandlung.]
Wolff, L. Lieb. Ann. Chem. 1912 394 (1), 86
The original paper by Ludwig Wolff on the reduction of aldehydes and ketones with hydrazine.
- The Wolff-Kishner Reaction of Hydrazones
Szmant, H. H.; Harmuth, C. H. Am. Chem. Soc.1964, 86 (14), 2909
A very nice Physical Organic study on the decomposition of hydrazones, involving Hammett plots (a classic tool in Physical Organic Chemistry), determining the relationship between the electron density of the carbonyl carbon and the mechanism.
- Reduction of Steroid Ketones and other Carbonyl Compounds by Modified Wolff-Kishner Method
Huang-Minlon Am. Chem. Soc.1949, 71 (10), 3301
A one-pot modification for the Wolff-Kishner reaction that involves distilling off the excess water and hydrazine before heating the hydrazine. This results improved yields and significantly shorter reaction times.
- REDUCTION OF KETONES BY USE OF THE TOSYLHYDRAZONE DERIVATIVES: ANDROSTAN-17 β-OL
Caglioti Org. Synth. 1972,52, 122
Due to the harsh conditions involved in the standard Wolff-Kishner reduction, a number of variations have been developed with milder conditions more amenable for organic synthesis. The use of tosylhydrazide instead of hydrazine allows much gentler reaction conditions – the tosylhydrazone can be reduced with NaBH4 in refluxing methanol (68 °C vs. 200 °C!).