Imine formation
Abstract
Imine formation involves the condensation of an aldehyde or a ketone with a primary amine, under Brønsted acid catalysis.
Keywords
Ketone, Aldehyde, Amine, Imine
Category
Aldehyde/Ketone, Amine
Mechanism
The reaction begins with protonation of the carbonyl oxygen by the Brønsted acid, increasing the electrophilicity of the carbonyl carbon. The amine then attacks this carbon, forming a protonated hemiaminal intermediate. After a proton transfer step, the hydroxyl group is protonated, converting it into a good leaving group. Elimination of water then occurs, leading to a iminium ion. Finally, deprotonation regenerates the acid catalyst and affords the neutral imine.
