Abstract
AbstractThe reactions of methyl α‐chloroacrylate (MCA) with organozinc compounds were studied. The elementary reactions of MCA with di‐n‐butylzinc (n‐Bu2Zn) in toluene and tetrahydrofuran (THF) were found to be conjugate addition and carbonyl addition reactions. n‐Butyl(dimethyl malonato)zinc (n‐BuZnDMM), on the other hand, underwent only conjugate addition reaction. Some parts of the conjugate addition products were transformed to cyclopropane derivatives.Methyl α‐chloroacrylate was found to be polymerized in toluene and THF with n‐Bu2Zn and n‐BuZnDMM as initiator. Results of some copolymerization reactions as well as kinetic studies indicated the mechanism of the polymerization in toluene or THF to be radical type. In hexamethylphosphoric triamide (HMPT), however, this monomer was polymerized through anionic mechanism. Any sign of the cyclopropane formation was not detected in HMPT as solvent even in the reaction with an excess of the organozinc compounds.
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