Cyclohexene epoxidation by the mono-oxygenase model (tetraphenylporphyrinato)manganese(III) acetate-sodium hypochlorite was written by Razenberg, J. A. S. J.;Van der Made, A. W.;Smeets, J. W. H.;Nolte, R. J. M.. And the article was included in Journal of Molecular Catalysis in 1985.Synthetic Route of C47H36N4O The following contents are mentioned in the article:
Oxidation of cyclohexene by (tetraphenylporphyrinato)manganese(III) acetate (I) and sodium hypochlorite as oxidant was studied in a two-phase H2O-CH2Cl2 system in the presence of a phase transfer reagent. A kinetic study with this system reveals the following features: the main product of the reaction (yield ¡Ý 80%) is 1,2-epoxycyclohexane; in the presence of excess oxidant the reaction is zero order in cyclohexene; the reaction order in Mn(III) concentration decreases from 1 to ? 0 with increasing concentration of this catalyst; the reaction order in hypochlorite decreases from 1 to 0 with increasing concentration of the reagent; pyridine and substituted pyridines enhance the reaction rate. A Hammett treatment of the rate data for various substituted pyridines gives a ¦Ñ-value of -1.00. Anchoring of I onto poly(vinylpyridine) or a polymer of an isocyanide increases the reaction rate by a factor of 1.5-6.0. Based on these findings and on evidence from the literature, a mechanism for the epoxidation of cyclohexene is proposed. The key intermediate is an oxo-manganese(V) complex, which is formed from Mn(III) and hypochlorite in a pyridine-catalyzed step. The Mn(V) species may react in 2 ways: either with substrate to give epoxide or with Mn(III) to form a ¦Ì-oxomanganese(IV) dimer. The latter route is suppressed when the catalyst is anchored to the polymeric support. This study involved multiple reactions and reactants, such as 4-(10,15,20-Tri-p-tolylporphyrin-5-yl)phenol (cas: 57412-08-5Synthetic Route of C47H36N4O).
4-(10,15,20-Tri-p-tolylporphyrin-5-yl)phenol (cas: 57412-08-5) belongs to catalyst ligands. Ligand, in chemistry, any atom or molecule attached to a central atom, usually a metallic element, in a coordination or complex compound. Precious metals and metal oxides on carrier materials are used in many industrial processes as heterogenous catalysts.Synthetic Route of C47H36N4O
Referemce:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI