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.

Additional recommended knowledge

Guide to balance cleaning: 8 simple steps

Weighing the right way

Better weighing performance in 6 easy steps

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

R₂C = CR − NR₂

See also

• Thorpe reaction