Abstract
The iron (III) complexes Fe (S)6(ClO4)3, S=solvent, were prepared from Fe (H2O)6(ClO4)3 in the donor solvents. Reactions of alkylbenzenes with Fe(AN)6(ClO4)3 (AN=acetonitrile) were explored because the AN complex has the highest formal redox potential, E°=1.73 V vs. SCE, among these complexes. Oxidation of the primary alkylbenzenes by the iron (III) AN complex gave the corresponding acetamides (Table II). Oxidation of the secondary alkylbenzenes, namely, cumene, 2-phenylbutane, and 2-exo-phenylnorborane, afforded the corresponding acetates and acetamides (Charts 2 and 3), consuming over 4 mol eq of reagent. Reactions of p-xylene and hexamethylbenzene with Fe (CH2=CHCN)6(ClO4)3 also yielded the amides 31a and 31b. These results demonstrate the applicability of the iron (III) AN complex as a powerful reagent to oxidize organic substrates which have onset potentials of anodic current of ca. 2.0 V vs. SCE.
