Oxidative cleavage of alkenes catalyzed by a water/organic soluble manganese porphyrin complex

Tetrakis(4-hydroxyphenyl)porphyrin [TPP–(OH)4] was modified with poly(ethylene glycol) chain as four side arms, such that this compound is soluble in both organic and water solutions. Complexation of this porphyrin with manganese metal ions resulted in the formation of MnCl–TPP–(PEO750)4. This complex proved to be an excellent catalyst for the oxidative cleavage of Cdouble bond; length as m-dashC bonds, yielding the corresponding carbonyl compounds with sodium periodate as an oxidant. Mechanistic pathway for this cleavage is discussed.