Aromatic Substitutions by Aryl Radicals. II

Substitutions of Nitrobenzene and Anisole by the p-Chlorophenyl Radical

Abstract

The determination, by means of isotope dilution analysis, of the molar ratio of p-chlorobiphenyl-³⁶Cl, 4-chloro-2′-nitrobiphenyl-³⁶Cl, 4-chloro-3′-nitrobiphenyl-³⁶Cl, 4-chloro-4′-nitrobiphenyl-³⁶Cl, 4-chloro-2′-methoxybiphenyl-³⁶Cl, 4-chloro-3′-methoxybiphenyl-³⁶Cl and 4-chloro-4′-methoxybiphenyl-³⁶Cl formed through the reaction of N-nitroso-p-chloroacetanilide-³⁶Cl in an equimolar mixture of nitrobenzene, anisole and benzene, is described. From the results, the partial rate factors of the ortho, meta and para, positions for the homolytic p-chlorophenylation were found to be 4.35, 0.61 and 6.18 for nitrobenzene and 3.93, 0.94 and 1.54 for anisole, respectively, the reactivity of the one position of benzene being taken as unity.