Transient Formation of N-Alkylhemins during Hemin-Catalyzed Epoxidation of Norbornene. Evidence Concerning the Mechanism of Epoxidation

Article abstract of DOI:10.1021/ja00246a019

During the course of hemin-catalyzed epoxidation of norbornene and other alkenes, the hemin catalyst is converted to N-alkylhemin by addition to the alkene.This transient species is a catalyst for epoxidation but is not an intermediate.As the oxidant disappears, the N-alkylhemin reverts to the original hemin.Proposed mechanisms that require the accumulation of other transients can be excluded because the N-alkylhemin is the only species that accumulates.