Topic summary
Enamine
An enamine is a functional group with the formula R2N−C(R′)=CR″2. Enamines are reagents used in organic synthesis and are intermediates in some enzyme-catalyzed reactions.
The word "enamine" is derived from the affix en-, used as the suffix of alkene, and the root amine. This can be compared with enol, which is a functional group containing both alkene (en-) and alcohol (-ol). Enamines are nitrogen analogs of enols.
Enamines are both good nucleophiles and good bases. Their behavior as carbon-based nucleophiles is explained with reference to the following resonance structures.