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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 reaction is occasionally called the Wolff-Schröter rearrangement. [2] The Wolff rearrangement was not commonly used until 20 years after it was discovered, as facile diazo ketone synthesis was unknown until the 1930s. [2] The reaction has proven useful in synthetic organic chemistry and many reviews have been published. [1] [2] Wolff's ...
The Knorr pyrrole synthesis is a widely used chemical reaction that synthesizes substituted pyrroles (3). [1] [2] [3] The method involves the reaction of an α-amino-ketone (1) and a compound containing an electron-withdrawing group (e.g. an ester as shown) α to a carbonyl group (2). [4] The Knorr pyrrole synthesis
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
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 ...
Ludwig Wolff (27 September 1857 – 24 February 1919), born in Neustadt in Palatinate, was a German chemist. [1] He studied chemistry at the University of Strasbourg, where he received his Ph.D. from Rudolph Fittig in 1882. He became Professor of analytical chemistry at the University of Jena in 1891 and held this position till his death in 1919.