Epoxidation of alkenes under liquid-liquid biphasic conditions: Synthesis and catalytic activity of Mn(III)-tetraarylporphyrins bearing perfluoroalkyl tails

Article abstract of DOI:10.1016/S0040-4020(97)00272-X

Four tetraarylporphyrins bearing one n-C₈F₁₇ chain on each meso-aryl group have been synthesized, The Mn(III)-complexes of these new compounds (Mn-1 - Mn-4) were used as catalysts in alkene epoxidations carried out under aqueous-organic biphasic conditions. High epoxide yields were obtained with catalysts in which, along with perfluoroalkyl chains, bulky substituents were present at appropriate positions. The expected general enhancement of stability and catalytic activity due to the electron-withdrawing effect of n-C₈F₁₇ substituents was not observed. However, Mn-4 was found to be an exceptionally active catalyst for NaOCl promoted epoxidation of poorly reactive linear α-alkenes.