Relative kinetics of the radical addition of benzyl bromide to unsaturated compounds

Abstract

The relative rate constants of the addition of the C6H5CH2 radical to unsaturated compounds CH2=CHX (X = C4H9, SiMe3, CF3, CO2Me, CN) were determined under the conditions of initiation by the Fe(CO)5 + DMF system or by benzoyl peroxide. Depending on the values of the relative addition rate constants, the monomers can be arranged into the following series (X): CF3≈C4H9<SiMe3<CO2Me<CN. The relatively nucleophilic character of the benzyl radical has been shown. It was found that under the initiation conditions by the Fe(CO)5 + DMF system, the addition stage proceeds by a free radical mechanism.