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Fe(II)tris(2-pyridylmethyl)amine complexes, Fe(II)−TPA, having different co-existing anions, [Fe(TPA)(MeCN)2](ClO4)2 (1), [Fe(TPA)(MeCN)2](CF3SO3)2 (2) and [Fe(TPA)Cl2] (3), were prepared. Effective magnetic moments (evaluated by the Evans method) revealed that while 1−3 in acetone and 3 in acetonitrile (MeCN) have a high-spin Fe(II) ion at 298 K, the Fe(II) ions of 1 and 2 are in the low-spin state in MeCN. The aerobic oxidation of 1−3 was monitored by UV−Vis spectral changes in acetone or MeCN under air at 298 K. Only the high-spin Fe(II)−TPA complexes were oxidized with rate constants of kobs = 0.1−1.3 h , while 1 and 2 were stable in MeCN. The aerobic oxidation of 1 or 2 in acetone was greatly accelerated in the presence of pure, peroxide-free cyclohexene (1000 equiv.) and yielded a large amount of oxidized products; 2-cyclohexe-1-ol (A) and 2-cyclohexene-1-one (K) (A+K: 23940% yield based on Fe; A/K = 0.3), and cyclohexene oxide (810%). Besides cyclohexene, aerobic oxidation of norbornene, cyclooctene, ethylbenzene, and cumene proceeded in the presence of 1 in acetone at 348 K without any reductant. Essential factors in the reaction are high-spin Fe(II) ion and labile coordination sites, both of which are required to generate Fe(II)-superoxo species as active species for the H-atom abstraction of hydrocarbons.

Studies on Catalytic Aerobic Oxidation of Organic Molecules: Development in Activation of Molecular Oxygen and Substrates