Catalytic activity and oxidative stability of a series of iron and manganese porphyrins with 2-chlorophenyl, phenyl and 4-methoxyphenyl at the meso positions and metallosalens (Mn-and Fe-salens) including N, N′-bis(salicylidene) ethylenediamine, N,N′-bis(5-chlorosalicylidene)ethylenediamine and N,N′-bis(2,4-dihydroxysalicylidene)ethylenediamine for the oxidation of olefins with tetra-n-butylammonium periodate (TBAP) and tetra-n-butyl-ammonium Oxone (TBAO) have been investigated and compared. Although the metalloporphyrins showed an increased catalytic activity relative to the Schiff base complexes, the former provided no significant catalytic advantage over the latter. Also, a comparable or slightly higher oxidative stability was observed for the Schiff base complexes under the reaction conditions. Furthermore, in spite of large difference between the oxidizing ability of TBAO and TBAP, similar patterns were observed for the order of catalytic activity and oxidative stability of the used heme and nonheme catalysts. The introduction of a methyl group at the ɑ position of styrene led to an increase in its reactivity, indicating the dominance of electronic effects over the steric ones in these catalytic systems.