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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 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 double bond of the side chain condensation product is reduced with sodium amalgam. The intermediate 4 is then converted to 2-methyl-5-hexylfuran 5 in a Wolff-Kishner reduction using hydrazine. An acid-catalyzed reaction at 120 °C (248 °F) cleaves the furan ring, producing 2,5-undecanedione 6. [1]
Darzens condensation, Darzens–Claisen reaction, Glycidic ester condensation; ... Wolff rearrangement; Wolff–Kishner reduction; Woodward cis-hydroxylation;
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 ...
The acylated reaction product can be converted into the alkylated product via a Clemmensen or a Wolff-Kishner reduction. [17] The Gattermann–Koch reaction can be used to synthesize benzaldehyde from benzene. [18] The Gatterman reaction describes arene reactions with hydrocyanic acid. [19] [20]
The Chichibabin pyridine synthesis (/ ˈ tʃ iː tʃ iː ˌ b eɪ b iː n /) is a method for synthesizing pyridine rings. The reaction involves the condensation reaction of aldehydes, ketones, α,β-Unsaturated carbonyl compounds, or any combination of the above, with ammonia. [1]
Reaction of cyclohexylamine with acetaldehyde forming an imine. Sodium sulfate removes water [1]. In organic chemistry, alkylimino-de-oxo-bisubstitution is the organic reaction of carbonyl compounds with amines to imines. [2]