Structural effects on the reactivity of carbon radicals in homolytic aromatic substitutions. Part III. Reaction of the 1-adamantyl radical with benzene derivatives

Abstract

Homolytic substitution of monosubstituted benzenes by 1-adamantyl radical has been carried out and the reactivity and the polar character of the radical have been determined by examining the effects of substituents on isomer distributions and on relative reactivities. The results indicated that the 1-adamantyl radical has nucleophilic properties which are more pronounced than that of other more strained bridgehead radicals; it is suggested that this behaviour is attributable to the different role played by polar effects during the addition of bridgehead radicals to aromatic substrates. The syntheses of several monosubstituted 1-aryladamantanes are also described.