Reactions of α-halo-α,β-unsaturated aldehydes with secondary amines

Article abstract of DOI:10.1007/bf01433745

Reactions of 2-halo-2-alkenals R″(R′)C=CX-CHO with secondary amines R₂NH occur as ipso-substitution of the halogen atom, along with fragmentation and condensation, yielding 1,2-diaminoethenes R₂NCH=CHNR₂, carbonyl compounds R″C(O)R′, 1,3-bis(amino)-2-haloolefins R″(R′)C(NR₂)CX=CHNR₂, and formamides R₂NCHO. The ratio between the competing reactions depends on the structure of the starting compounds and the experimental conditions.