Multistep nucleophilic substitution of the halogen atom in 2-halo-2-alkenals

Article abstract of DOI:10.1007/BF01433746

ipso-Substitution of the halogen atom in 2-halo-2-alkenals under the action of secondary amines proceeds via three consecutive steps: addition, nucleophilic substitution, and β-elimination (the Ad_N-S_N-E mechanism). The main intermediates arising in the reactions of 2-chloropropenal and 2-chloro-2-butenal with piperidine were detected by NMR spectroscopy. A general scheme of the reaction is proposed.