Abstract
The term “enamines” refers to the compounds containing both an amino group and a double bond. Substituted vinylic amines may be obtained by reacting various carbonyl compounds with pyrrolidine. The enamine obtained in this way is an important synthetic intermediate. This is because of the nucleophilic character of enamines. Stork has shown that compounds of this type may be used for the monoalkylation of ketones without the production of accompanying di- and poly-alkylated products that would be obtained by the direct alkylation of the free ketones. The base removes a proton from the position α- to the carbonyl group, and the carbanion, thus, obtained attacks the alkyl halide. It is easier to remove a proton from a tertiary carbon than from a secondary carbon atom. The C-Acylation of the carbon atom α-to the carbonyl group is equally possible by using an acid chloride and an enamine. This affords a good method for synthesizing β-diketones.
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