Free-radical substitution in aliphatic compounds. Part XVIII. The gas-phase chlorination of 1-phenylpropane

Abstract

The chlorination of 1-phenylpropane has been studied in the gas phase from 90–200°. Attack is favoured at the 1-position, while the 2-position is deactivated in comparison to the secondary positions in butane. Appreciable yields of 1-phenylprop-1-ene are formed. The amount of olefinic product was reduced by the addition of an inert gas (SF₆). It is suggested that when an alkyl radical reacts with molecular chlorine a thermally excited alkyl chloride is formed which, in cases where elimination is favoured, may lose hydrogen chloride.