Aromatic Substitutions by Aryl Radicals. VI:Substitutions of Nitrobenzene and Chlorobenzene by the p-Nitrophenyl Radical

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The determination, by means of isotope dilution analysis, of the molar ratio of p-nitrobiphenyl-14C, 2, 4′-dinitrobiphenyl-14C, 3, 4′-dinitrobiphenyl-14C, 4, 4′-dinitrobiphenyl-14C, 2-chloro-4′-nitrobiphenyl-14C, 3-chloro-4′-nitrobiphenyl-14C and 4-chloro-4′-nitrobiphenyl-14C formed through the reaction of N-nitrosop-nitroacetanilide-(pheny1-14C) in an equimolar mixture of nitrobenzene, chlo-robenzene and benzene, is described. From the results, the partial rate factors of the ortho, meta and para positions for the homolytic p-nitrophenylation were found to be 0.93, 0.35 and 1.53 for nitrobenzene and 1.53, 0.65 and 1.01 for chlorobenzene, respectively, the reactivity of the one position of benzene being taken as unity.
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