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Clemmensen Reduction
Clemmensen reduction is one of the well-known reductions to convert ketones and aldehydes to methylene moieties by the treatment of zinc under acidic conditions. Zinc amalgam was used in the first report, but there was difficulty in the treatment after the reaction due to highly harmful mercury. Since then, Yamamura’s group developed a modified non-aqueous condition using zinc powder and hydrogen chloride in an organic solvent. Since this condition usually does not require heat conditions, heat-labile substances can be applicable. Clemmensen reduction and Wolff-Kishner reduction are operated under acidic and basic conditions, respectively, so the two reactions can be used complementarily.
- Reagents:
- Zinc (Powder), Inorganic acids
- Reactants:
- Ketones, Aldehydes
- Products:
- Methylenes
- Scheme:
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- Original literature:
-
- Reduktion von Ketonen und Aldehyden zu den entsprechenden Kohlenwasserstoffen unter Anwendung von amalgamiertem Zink und Salzsäure
- Über eine allgemeine Methode zur Reduktion der Carbonylgruppe in Aldehyden und Ketonen zur Methylengruppe
- Über eine allgemeine Methode zur Reduktion der Carbonylgruppe in Aldehyden und Ketonen zur Methylengruppe. (III. Mitteilung.)
- Review literature:
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- The role of zinc carbenoids in organic synthesis
- Clemmensen Reduction of Ketones in Anhydrous Organic Solvents
