Imine - Imine Reactions

Imine Reactions

The most important reactions of imines are their hydrolysis to the corresponding amine and carbonyl compound. Otherwise this functional group participates in many other reactions, many of which are analogous to the reactions of aldehydes and ketones.

• An imine reacts with an amine to an aminal, see for example the synthesis of cucurbituril.
• An imine reacts with dienes in the Aza Diels-Alder reaction to a tetrahydropyridine.
• An imine can be oxidized with meta-chloroperoxybenzoic acid (mCPBA) to give an oxaziridine
• An aromatic imine reacts with an enol ether to a quinoline in the Povarov reaction.
• A tosylimine reacts with an α,β-unsaturated carbonyl compound to an allylic amine in the Aza-Baylis–Hillman reaction.
• Imines are intermediates in the alkylation of amines with formic acid in the Eschweiler-Clarke reaction.
• A rearrangement in carbohydrate chemistry involving an imine is the Amadori rearrangement.
• A methylene transfer reaction of an imine by an unstabilised sulphonium ylide can give an aziridine system.
• An imine is an intermediate in reductive amination.