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Please login or sign up for a free trial to access the full content.48.1.3.1.3 Method 3: The Wolff–Kishner Reduction (Reduction of Aldehydes and Ketones via Hydrazones)
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Wicha, J., Science of Synthesis, (2009) 48, 111.
Base-induced fragmentation of hydrazones 21 or the corresponding semicarbazones 22, first reported by Kishner[103] and Wolff[104] (the Wolff–Kishner reduction), provides a convenient method for obtaining hydrocarbons from aldehydes or ketones (Scheme 25). Synthetic applications of the Wolff–Kishner reduction have been extensively reviewed in Houben–Weyl, Vol. 5/1a, pp 251, 544 and Vol. 7/2b, p 1999 and in other compendia.[6,105–107] In the original Kishner procedure,[103] the transformation is accomplished by dropping a hydrazone onto hot potassium hydroxide, with which some crushed platinized porous plate has been mixed. In the method reported by Wolff,[104] a hydrazone or semicarbazone and sodium ethoxide are heated in a sealed tube at 180°C. It has been proven that the semicarbazone undergoes hydrolysis or alcoholysis with formation of the corresponding hydrazone in the initial step.
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References
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- 8.Meeeee-Meee, (8888) M 88e8, 888.
- 8.Meeeee-Meee, (8888) M 8e, 88.
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