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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.
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 ...
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.
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