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The Wolff–Kishner reduction is a reaction used in organic chemistry to convert carbonyl functionalities into methylene groups. [1] [2] 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.
The molecular formula C 5 H 6 S may refer to: Methylthiophenes. 2-Methylthiophene, an organosulfur compound that can be produced by Wolff-Kishner reduction of thiophene-2-carboxaldehyde; 3-Methylthiophene, an organosulfur that can be produced by sulfidation of 2-methylsuccinate; Thiopyran, a heterocyclic compound
Mechanism of Wolff-Kishner reduction. Aromatic carbonyls are more readily reduced to their respective alkanes than aliphatic compounds. [26] For example, ketones are reduced to their respective alkyl benzenes by catalytic hydrogenation [27] [28] or by Birch reduction [29] under mild conditions.
The Seyferth–Gilbert homologation is a chemical reaction of an aryl ketone 1 (or aldehyde) with dimethyl (diazomethyl)phosphonate 2 and potassium tert-butoxide to give substituted alkynes 3.
Even with the development of other variants of the Wolff-Kishner reaction, it remains a widely practiced version of the reaction today. Some other practical advantages include the simple experimental setup, inexpensive starting materials, and a reduced amount of solvent needed, factors which made the conditions suitable for use in China at the ...
The Wharton olefin synthesis or the Wharton reaction is a chemical reaction that involves the reduction of α,β-epoxy ketones using hydrazine to give allylic alcohols. [1] [2] [3] This reaction, introduced in 1961 by P. S. Wharton, is an extension of the Wolff–Kishner reduction.
Wolff–Kishner reduction: Alkane: If an aldehyde is converted to a simple hydrazone (RCH=NHNH 2) and this is heated with a base such as KOH, the terminal carbon is fully reduced to a methyl group. The Wolff–Kishner reaction may be performed as a one-pot reaction, giving the overall conversion RCH=O → RCH 3. Pinacol coupling reaction: Diol
Hydrazones are intermediates in the Wolff–Kishner reduction. Hydrazones are reactants in hydrazone iodination, the Shapiro reaction, and the Bamford–Stevens reaction to vinyl compounds. Hydrazones can also be synthesized by the Japp–Klingemann reaction via β-keto acids or β-keto-esters and aryl diazonium salts.