Enamine

File:Enamine-2D-skeletal.pngThe general structure of an enamine

An enamine is an unsaturated compound derived by the reaction of an aldehyde or ketone with a secondary amine followed by loss of H2O.

The word "enamine" is apparently derived from the prefix en-, used as the suffix of alkene, and the root amine. Compare with enol, which is a molecule containing both alkene (en-) and alcohol (-ol).[citation needed]

If one of the nitrogen substituents is H, it is the tautomeric form of an imine. This usually will rearrange to the imine; however there are several exceptions (such as aniline). The enamine-imine tautormerism may be considered analogous to the keto-enol tautomerism. In both cases, a hydrogen atom switches its location between the heteroatom (oxygen or nitrogen) and the second carbon atom.

## Form

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<math>R_2C=CR-NR_2</math>

## See also

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* Thorpe reaction

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