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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.
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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]
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.
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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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