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- Wolff–Kishner_reduction abstract "The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step. As such, there is no obvious retron for this reaction. Originally reported by Nikolai Kischner in 1911 and Ludwig Wolff in 1912, it has been applied to the total synthesis of scopadulcic acid B, aspidospermidine and dysidiolide.In general, the reaction mechanism first involves the in situ generation of a hydrazone by condensation of hydrazine with the ketone or aldehyde substrate. Sometimes it is however advantageous to use a pre-formed hydrazone as substrate (see modifications). The hydrazone is deprotonated by alkoxide base followed by a concerted, rate-determining step in which a diimide anion is formed. Collapse of this alkyldiimde with loss of N2 leads to formation of an alkylanion which can be protonated by solvent to give the desired product.Because the Wolff–Kishner reduction requires highly basic conditions, it is unsuitable for base-sensitive substrates. However, this method can be superior over the related Clemmensen reduction for acid-sensitive compounds such as pyrroles and for high-molecular weight compounds.".
- Wolff–Kishner_reduction thumbnail Wolff-Kishner-reaction_scheme-new.png?width=300.
- Wolff–Kishner_reduction wikiPageID "1216247".
- Wolff–Kishner_reduction wikiPageRevisionID "601555142".
- Wolff–Kishner_reduction subject Category:Name_reactions.
- Wolff–Kishner_reduction subject Category:Organic_redox_reactions.
- Wolff–Kishner_reduction comment "The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. In the context of complex molecule synthesis, it is most frequently employed to remove a carbonyl group after it has served its synthetic purpose of activating an intermediate in a preceding step. As such, there is no obvious retron for this reaction.".
- Wolff–Kishner_reduction label "Reação de Wolff-Kischner".
- Wolff–Kishner_reduction label "Reducción de Wolff-Kishner".
- Wolff–Kishner_reduction label "Redukcja Wolffa-Kiżnera".
- Wolff–Kishner_reduction label "Riduzione di Wolff-Kishner".
- Wolff–Kishner_reduction label "Réduction de Wolff-Kishner".
- Wolff–Kishner_reduction label "Wolff-Kishner-Reaktion".
- Wolff–Kishner_reduction label "Wolff-Kishner-reductie".
- Wolff–Kishner_reduction label "Wolff–Kishner reduction".
- Wolff–Kishner_reduction label "Реакция Кижнера — Вольфа".
- Wolff–Kishner_reduction label "ウォルフ・キッシュナー還元".
- Wolff–Kishner_reduction label "沃尔夫-凯惜纳-黄鸣龙还原反应".
- Wolff–Kishner_reduction sameAs Wolff%E2%80%93Kishner_reduction.
- Wolff–Kishner_reduction sameAs Wolffova-Kižněrova_redukce.
- Wolff–Kishner_reduction sameAs Wolff-Kishner-Reaktion.
- Wolff–Kishner_reduction sameAs Reducción_de_Wolff-Kishner.
- Wolff–Kishner_reduction sameAs Réduction_de_Wolff-Kishner.
- Wolff–Kishner_reduction sameAs Riduzione_di_Wolff-Kishner.
- Wolff–Kishner_reduction sameAs ウォルフ・キッシュナー還元.
- Wolff–Kishner_reduction sameAs Wolff-Kishner-reductie.
- Wolff–Kishner_reduction sameAs Redukcja_Wolffa-Kiżnera.
- Wolff–Kishner_reduction sameAs Reação_de_Wolff-Kischner.
- Wolff–Kishner_reduction sameAs Q281381.
- Wolff–Kishner_reduction sameAs Q281381.
- Wolff–Kishner_reduction wasDerivedFrom Wolff–Kishner_reduction?oldid=601555142.
- Wolff–Kishner_reduction depiction Wolff-Kishner-reaction_scheme-new.png.