Polychlorobenzenes, polybromobenzenes, and polychloropolybromobenzenes (C6H6−nXn) were photolyzed in benzene solutions; the products were analyzed by the GC/MS method. Both dehalogenation and phenylation were shown to take place competitively, producing (poly)halobenzenes bearing one less halogen atom (C6H7−nXn−1) and (poly)halobiphenyls (C6H6−nXn−1–C6H5) as the major products. Besides these products, terphenyl was produced by a consecutive phenylation of the halobiphenyl formed. Polychlorobenzenes were shown to form the corresponding terphenyls only when a pathway via 2-chlorobiphenyl is possible; however, polybromobenzenes can produce terphenyls through any of the isomeric bromobiphenyls intermediarily formed. Isomerization through m-migration of a chlorine atom was also shown to occur to a considerably lesser extent.
073ChemInform Abstract Dehalogenation and phenylation take place competitively in the photoreaction of polyhalobenzenes such as (I), (VII), and (XII). The preference for phenylation is more significant in the case of chlorinated benzenes. In contrast to the bromobenzenes, the chloro analogues form terphenyls only when a pathway via 2-chlorobiphenyl is possible.
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