А. V. Zorin, A. T. Zaynashev, V. Zorin
Apr 1, 2021
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Journal
Russian Journal of General Chemistry
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.