Reactions of Alkyl 2-(Bromozinc)acylates with N-Chloro- and N-Bromodiethylamines

Abstract The reaction of alkyl 2-(bromozinc)acylates, obtained from ethyl bromoacetate (or butyl 2-bromobutanoate, or butyl 2-bromo-2-methylpropanoate) under the action of zinc, with N-chloro- or N-bromodiethylamine in tetrahydrofuran at 20–25°C under argon for 2 h resulted in the formation of diethyl succinate (or dibutyl 2,3-diethyl succinate, or dibutyl tetramethyl succinate) and diethylamine instead of the expected products of the nucleophilic substitution of the halogen with the 2-alkoxycarbonylalkyl residue. An anion-radical reaction mechanism was proposed.