Aromatic Substitutions by Aryl Radicals. III:Substitutions of Toluene and Chlorobenzene by the p-Chlorophenyl Radical

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The determination of the molar ratio of p-chlorobiphenyl-36Cl, 4-chloro-2′-methylbiphenyl-36Cl, 4-chloro-3′-methylbiphenyl-36Cl and 4-chloro-4′-methylbiphenyl-36C1 formed through the reaction of N-nitroso-p-chloroacetanilide-36Cl in an equimolar mixture of toluene and benzene is described. From the results, the partial rate factors of the ortho, meta and para positions of toluene for the homolytic p-chlorophenylation were found to be 2.97, 1.07 and 1.32, respectively. Partial rate factors for chlorobenzene, 2.70, 0.86 and 1.33 were obtained from the results of experiments in a mixture of chlorobenzene and benzene. From the sequence of the relative reactivities of meta positions of aromatic compounds, it is suggested that the p-chlorophenyl radical has electrophilic character.
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