Enamine

An enamine is a type of unsaturated chemical compound derived from the condensation of an aldehyde or a ketone with a secondary amine. Enamines are nitrogen analogs of enols, exhibiting a carbon-carbon double bond adjacent to an amine group. They are important intermediates in organic synthesis, notably in reactions such as the Stork enamine alkylation. The nitrogen atom on the enamine can be attached to two alkyl or aryl groups, and it must be a secondary amine derivative for enamine formation to occur. Primary amines react to form imines (also known as Schiff bases), and tertiary amines cannot react as they lack a proton that can be removed. Enamines are generally more nucleophilic than enols due to the electron-donating effect of the nitrogen atom. The double bond in an enamine is electron-rich and can react with electrophiles. Enamines are often hydrolyzed in acidic conditions to regenerate the carbonyl compound and the secondary amine.