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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.
Structure of the hydrazone functional group. Hydrazones are a class of organic compounds with the structure R 1 R 2 C=N−NH 2. [1] They are related to ketones and aldehydes by the replacement of the oxygen =O with the = N−NH 2 functional group. They are formed usually by the action of hydrazine on ketones or aldehydes. [2] [3]
The reaction mechanism of the Mitsunobu reaction is fairly complex. The identity of intermediates and the roles they play has been the subject of debate. Initially, the triphenyl phosphine (2) makes a nucleophilic attack upon diethyl azodicarboxylate (1) producing a betaine intermediate 3, which deprotonates the carboxylic acid (4) to form the ion pair 5.
Hemiacetals form in the reaction between alcohols and aldehydes or ketones. Using an acid catalyst, the reaction proceeds via nucleophilic attack of the carbonyl group by the alcohol. [4] A subsequent nucleophilic attack of the hemiacetal by the alcohol results in an acetal. [2] Solutions of simple aldehydes in alcohols mainly consist of the ...
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 .
In organic chemistry, aldol reactions are acid- or base-catalyzed reactions of aldehydes or ketones. Aldol addition or aldolization refers to the addition of an enolate or enolation as a nucleophile to a carbonyl moiety as an electrophile. This produces a β-hydroxyaldehyde or β-hydroxyketone.
Alcohol oxidation is a collection of oxidation reactions in organic chemistry that convert alcohols to aldehydes, ketones, carboxylic acids, and esters. The reaction mainly applies to primary and secondary alcohols. Secondary alcohols form ketones, while primary alcohols form aldehydes or carboxylic acids. [1] A variety of oxidants can be used.
Finally, the alkylated ketone or aldehyde can be regenerated by ozonolysis or hydrolysis. [3] Enders' SAMP/RAMP Hydrazone Alkylation Reaction. This reaction is a useful technique for asymmetric α-alkylation of ketones and aldehydes, which are common synthetic intermediates for medicinally interesting natural products and other related organic ...