Synthesis and remarkable properties of iron β-polynitroporphyrins as catalysts for monooxygenation reactions

Abstract

Two new porphyrins bearing several electron-withdrawing β-substituents were obtained in one step, in yields of about 50%, by nitration of meso-tetra(2,6-dichlorophenyl)porphyrin (TDCPPH₂) and meso-tetrapentafluorophenylporphyrin (TFPPH₂) with HNO₃; the iron(III) complex of β-hexanitro-TDCPPH₂ was a remarkable catalyst for the epoxidation of cyclooctene with diluted H₂O₂(complete conversion and 97% yield in 0.5 h) in the absence of any cocatalyst, and for the hydroxylation of alkanes, e.g. heptane, by O₂.