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Enamine
 
 
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An enamine is an unsaturated
Saturation (chemistry)

In chemistry, saturation has five different meanings:#In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of it will appear as a Precipitation ....
 compound derived by the reaction of an aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
 or ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
 with a secondary amine followed by loss of H2O.

The word "enamine" is derived from the prefix en-, used as the suffix of alkene
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
, and the root amine
Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
.






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Enamine 2d Skeletal
An enamine is an unsaturated
Saturation (chemistry)

In chemistry, saturation has five different meanings:#In physical chemistry, saturation is the point at which a solution of a substance can dissolve no more of that substance and additional amounts of it will appear as a Precipitation ....
 compound derived by the reaction of an aldehyde
Aldehyde

An aldehyde is an organic compound containing a terminal carbonyl group. This functional group, which consists of a carbon atom bonded to a hydrogen atom and double bond to an oxygen atom , is called the aldehyde group....
 or ketone
Ketone

In organic chemistry, a ketone is a type of organic compound which contains a carbonyl group bonded to two other carbon atoms in the form:Neither of the substituents R1 and R2 may be equal to hydrogen ....
 with a secondary amine followed by loss of H2O.

The word "enamine" is derived from the prefix en-, used as the suffix of alkene
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
, and the root amine
Amine

Amines are organic compounds and functional groups that contain a base nitrogen atom with a lone pair. Amines are derivative s of ammonia, wherein one or more hydrogen atoms are replaced by organic substituents such as alkyl and aryl groups....
. Compare with enol
Enol

Enols are alkenes with a hydroxyl group affixed to one of the carbon atoms composing the double bond. Enols and carbonyl compounds are in fact isomers; this is called keto-enol tautomerism:...
, which is a molecule containing both alkene
Alkene

In organic chemistry, an alkene, olefin, or olefine is an Saturation chemical compound containing at least one carbon-to-carbon double bond....
 (en-) and alcohol
Alcohol

In chemistry, an alcohol is any organic compound in which a hydroxyl Functional group is bound to a carbon atom of an alkyl or substituted alkyl group....
 (-ol).

If one of the nitrogen substituents is H, it is the tautomer
Tautomer

Tautomers are isomers of organic compounds that readily interconvert by a chemical reaction called tautomerization. Commonly this reaction results in the formal migration of a hydrogen atom or proton, accompanied by a switch of a single bond and adjacent double bond....
ic form of an imine
Imine

An imine is a functional group or chemical compound containing a carbon?nitrogen double bond . Due to their diverse reactivity, imines are common substrates in a wide variety of transformations....
. This usually will rearrange to the imine; however there are several exceptions (such as aniline
Aniline

Aniline, phenylamine or aminobenzene is an organic compound with the Chemical formula C6H7N. It is the simplest and one of the most important aromatic amines, being used as a precursor to more complex chemicals....
). The enamine-imine tautormerism may be considered analogous to the keto-enol tautomerism
Keto-enol tautomerism

In organic chemistry, keto-enol tautomerism refers to a chemical equilibrium between a keto form and an enol. The enol and keto forms are said to be tautomers of each other....
. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom.

See also

  • Thorpe reaction
    Thorpe reaction

    The Thorpe reaction is a chemical reaction described as a self-condensation of aliphatic nitriles catalyzed by Base to form enamines. The reaction was discovered by Jocelyn Field Thorpe....