CYCLOHEXENE EPOXIDATION BY THE MONO-OXYGENASE MODEL (TETRAPHENYLPORPHYRINATO)MANGANESE(III) ACETATE-SODIUM HYPOCHLORITE.

Article abstract of DOI:10.1016/0304-5102(85)85110-5

Oxidation of cyclohexene by (tetraphenylporphyrinato)manganese(III) acetate (Mn(TPP)OAc) and sodium hypochlorite as oxidant has been studied in a two-phase water-dichloromethane system in the presence of a phase transfer reagent. A kinetic study with this system reveals the following features: (1) the main product of the reaction (yield greater than equivalent to 80%) is 1,2-epoxy-cyclohexane; (2) in the presence of excess oxidant the reaction is zero order in cyclohexene; (3) the reaction order in Mn(III) concentration decreases from 1 to approximately equals 0 with increasing concentration of this catalyst; (4) the reaction order in hypochlorite decreases from 1 to 0 with increasing concentration of this reagent; (5) pyridine and substituted pyridines enhance the reaction rate. A mechanism for the epoxidation of cyclohexene is proposed.