Free-Radical Mechanisms in the Oxidation and Halogenation of Alkanes, Alkenes and Alkylbenzenes by t-BuOOH under Gif-Barton Catalysis

A considerable effort has been carried out to show the non-radical character of the so-called "Gif reaction". Chemical and kinetic evidences and new synthetic developments, concerning the free-radical functionalization of alkanes, alkenes and alkylbenzenes by t-BuOOH under Gif conditions, are reported. The factors, which determine the specificity of the Gif reaction, are discussed, also in relation to other catalytic transition metal salt complexes (Kharasch synthesis of peroxides and metalloporphyrin catalysis).