SODIUM HYPOCHLORITE: A CONVENIENT OXYGEN SOURCE FOR OLEFIN EPOXIDATION CATALYZED BY (PORPHYRINATO)MANGANESE COMPLEXES.

Article abstract of DOI:10.1021/ja00334a035

A new catalytic route is reported for the epoxidation of simple olefins with NaOCl as oxygen source and manganese porphyrin complexes as catalyst. Reaction rate, chemoselectivity, and stereoselectivity are largely increased by the presence of pyridine which behaves as an axial ligand of the metalloporphyrin. Thus modified, the catalytic system is highly efficient for the epoxidation of di-, tri-, and tetrasubstituted olefins (yields, 60-95%). Aliphatic olefins are stereospecifically epoxidized (syn addition of the oxygen atom), while cis-stilbene gives a mixture of cis- and trans-epoxides. In the latter case, an increase of stereoselectivity up to 94% is observed in the presence of pyridine.