Catalytic epoxidation of cis-stilbene and naphthalene by tetra-n-butylammonium hydrogen monopersulfate in the presence of manganese(III) tetraarylporphyrins and various anionic co-catalysts

The epoxidation of cis-stilbene by n-Bu4NHSO5 was studied in the presence of two different manganese porphyrin complexes, [MnTPFPP(Cl) and MnTPP(Cl)], and various n-Bu4NX (X = OAc, F, Cl, Br, OCN, NO3, BF4). In general direct correlation was found between stereoselectivity of the epoxidation reaction and the nucleophilic properties of these anionic co-catalysts. Also epoxidation of naphthalene was carried out in high yield and good selectivity by n-Bu4NHSO5 in the presence of MnTPFPP(Cl) in association with n-Bu4NOAc or n-Bu4NF co-catalysts.