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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.
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 4-acetyl group could easily be converted to a 4-ethyl group by Wolff-Kishner reduction (hydrazine and alkali, heated); hydrogenolysis, or the use of diborane. Benzyl or tert-butyl acetoacetates also work well in this system, and with close temperature control, the tert-butyl system gives a very high yield (close to 80%). [10]
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; Z. Zinin reaction This page was last edited on 30 August 2021, at 11:23 (UTC). Text is available under the Creative Commons Attribution ...
In 1910 he described the catalytic decomposition of alcylidenhydrazines, which was later named as the Wolff–Kishner reduction. [1] [3] [4] In 1912, Kischner later applied the catalytic decomposition to pyrazoline bases and developed a versatile method for the preparation of substituted cyclopropanes by thermal decomposition of pyrazolines.
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 vinylogous Wolff rearrangement consists of a β,γ-unsaturated diazo ketone undergoing a Wolff rearrangement, and a formal 1,3-shift of the CH 2 CO 2 R group. The vinylogous Wolff rearrangement yields a γ,δ-unsaturated carboxylic acid derivative, which is the same retron as for the Claisen rearrangement. The variant was discovered when it ...