In this Stork enamine reaction, cyclohexanone is reacted with pyrrolidine in the presence of p-TsOH catalysis to produce an enamine. This enamine undergoes.

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Alkylation of an Enamine Enamined undergo an S N 2 reaction with reactive alkyl halides to give the iminium salt. The imine is then reacted with an Grignard reagent to the corresponding magnesium salt to an intermediate capable of displacing a halide.

Organic Chemistry Hardcover 6th ed. This page was last edited on 6 Aprilat Michael Addition using Enamines Enamines, like other weak bases, add 1,4 to enones.

Stork Enamine Reaction – ChemistryScore

Because of this enamines can be used as synthetic equivalents as enolates in many reactions. Enamines act as nucleophiles in a fashion similar to enolates.


These reactions are generally known as the Stork enamine reaction after Gilbert Stork of Columbia University who originated the work.

When the electrophile is an acyl halidea 1,3- diketone is formed Stork acylation.

Some of the advantages of using an enamine over and enolate are enamines are neutral, easier to prepare, and usually prevent the overreaction problems plagued by storl. Carbon-carbon bond forming reactions Name reactions.

Enamine Reactions – Chemistry LibreTexts

By using this site, you agree to the Terms of Use and Privacy Policy. From Wikipedia, the free encyclopedia. In other projects Wikimedia Commons. The iminium salt can be hydrolyzed back into the carbonyl. Formation of an enamine Step 2: The Stork enamine alkylationinvolves the addition of an enamine to an alpha, beta-unsaturated carbonyl acceptor in a process similar to the Michael reaction.

As previously seen, aldehydes and ketones react with 2 enaine amines to reversibly form enamines. Steven Farmer Sonoma State University.

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This process requires a three steps: In this method a carbonyl compound is converted to an imine by alkylimino-de-oxo-bisubstitution with a primary amine. Enamined undergo an S N 2 reaction with reactive alkyl halides to give the iminium salt.

Views Read Edit View history. Use dmy dates from June Retrieved from ” https: Reactions, Mechanisms, and Structure 3rd ed. The end product is a 1,5 dicarbonyl compound.

Enamines, like other weak bases, add 1,4 to enones. In a special case of this reaction type it is also possible to alkylate ketones or aldehydes with alkyl halides as less reactive electrophiles: Hydrolysis once again yields the alkylated ketone.