enamine n : an amine containing the double bond linkage -C=C-N-

English

Noun

1. Any of a class of unsaturated nitrogen compounds, having the general formula R2C=C(R)-NR2, prepared by the condensation reaction of an aldehyde or ketone with an secondary amine; they are the tautomeric forms of imines.

See also

• ynamine

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).

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

R_2C=CR-NR_2

See also

• Thorpe reaction