Amines acting as hydride ion donors in reactions with unsaturated electrophilic compounds

The reactions involving reduction of electrophilic double bonds (C=C, C=O, C=N, and N=N) with amines (usually tertiary) that contain hydrogen atoms at the α-position have been classified. The key stage in such reactions is formation of an iminium salt, which can formally be regarded as the transfer of a hydride ion from the amine to the compound with a double bond, although the actual mechanism may be different. The subsequent reactions of the intermediates formed (iminium cations, enamines, aminocarbenes), including acylation and cycloaddition, are examined. The synthetic potentialities of these reactions for obtaining different functionally substituted linear and heterocyclic compounds are discussed.
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