Collect. Czech. Chem. Commun. 1990, 55, 2949-2955

Reactivity of substituted styrenes in the catalytic addition reaction with the trichloromethyl radical

Milan Hájek, Přemysl Šilhavý and Božena Špirková

Institute of Chemical Process Fundamentals, Czechoslovak Academy of Sciences, 165 02 Prague 6-Suchdol


Relative reactivities have been investigated in the catalytic addition of tetrachloromethane to substituted styrenes by the competitive method. The polar effects of substituents on benzene ring were correlated with Hammett equation for a copper and ruthenium catalyst, giving ρ values equal to -0.39 and -0.18 respectively. The results indicate that in contrast to classical additions the catalytic addition of tetrachloromethane is not a free radical chain process but that the trichloromethyl radical, presumably coordinated, reacts with the carbon-carbon double bond via innersphere pathways.