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 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 considered to be nitrogen analogs of enols.

If one of the nitrogen substituents is a hydrogen atom, 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 tautomerism 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.

Enamines are both good nucleophiles and good bases.

Other articles related to "enamine":

Asymmetric Mannich Reactions
... Proline enters a catalytic cycle by reacting with the aldehyde to form an enamine ... The two reactants (imine and enamine) line up for the Mannich reaction with Si facial attack of the imine by the Si-face of the enamine-aldehyde ... Relief of steric strain dictates that the alkyl residue R of the enamine and the imine group are antiperiplanar on approach which locks in the syn mode of addition ...
Stork Enamine Alkylation
... Stork enamine alkylation, also known as the Stork-Enamine reaction, involves the addition of an enamine to an alpha, beta-unsaturated carbonyl acceptor in a process similar to ... The process formation of an enamine from a ketone addition of the enamine to an alpha, beta-unsaturated aldehyde or ketone hydrolysis of the enamine back to ...
Leimgruber–Batcho Indole Synthesis - Reaction Mechanism
... In the initial enamine formation, dimethylamine (a gas) is displaced by pyrrolidine from the dimethylformamide dimethylacetal, producing a more reactive reagent ... conditions, and the resultant carbanion attacks to produce the enamine shown, with loss of methanol ... without the pyrrolidine, via the N,N-dimethyl enamine, though reaction times may be much longer in some cases ...
Chichibabin Pyridine Synthesis - Synthetic Applications - Limitations
1.Nucleophillic attack of ammonia at the β-, rather than α-carbon will prevent enamine/imine formation 2.Nucleophilic attack of ammonia on the enamine or imine 4.Enolate ion attack of the enamine or imine carbon 7 ... Immine attack at an enamine or imine carbon ...