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- Q281381 subject Q7458901.
- Q281381 subject Q8703541.
- Q281381 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.".
- Q281381 thumbnail Wolff-Kishner-reaction_scheme-new.png?width=300.
- Q281381 wikiPageWikiLink Q11351.
- Q281381 wikiPageWikiLink Q1990872.
- Q281381 wikiPageWikiLink Q201479.
- Q281381 wikiPageWikiLink Q2409792.
- Q281381 wikiPageWikiLink Q249087.
- Q281381 wikiPageWikiLink Q281381.
- Q281381 wikiPageWikiLink Q334640.
- Q281381 wikiPageWikiLink Q410125.
- Q281381 wikiPageWikiLink Q416007.
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- Q281381 wikiPageWikiLink Q418193.
- Q281381 wikiPageWikiLink Q420630.
- Q281381 wikiPageWikiLink Q421902.
- Q281381 wikiPageWikiLink Q5609896.
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- Q281381 wikiPageWikiLink Q5925645.
- Q281381 wikiPageWikiLink Q730606.
- Q281381 wikiPageWikiLink Q74031.
- Q281381 wikiPageWikiLink Q7458901.
- Q281381 wikiPageWikiLink Q7485453.
- Q281381 wikiPageWikiLink Q7553383.
- Q281381 wikiPageWikiLink Q7827911.
- Q281381 wikiPageWikiLink Q7990731.
- Q281381 wikiPageWikiLink Q846597.
- Q281381 wikiPageWikiLink Q8703541.
- Q281381 wikiPageWikiLink Q898238.
- Q281381 wikiPageWikiLink Q898480.
- Q281381 wikiPageWikiLink Q898552.
- Q281381 wikiPageWikiLink Q898645.
- Q281381 wikiPageWikiLink Q900838.
- Q281381 wikiPageWikiLink Q901637.
- Q281381 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.".
- Q281381 label "Wolff–Kishner reduction".
- Q281381 depiction Wolff-Kishner-reaction_scheme-new.png.