On the mechanism of catalytic alkene oxidation by molecular oxygen and halogenated iron porphyrins

✍ Scribed by Eva R. Birnbaum; Mark W. Grinstaff; Jay A. Labinger; John E. Bercaw; Harry B. Gray

• Publisher: Elsevier Science
• Year: 1995
• Tongue: English
• Weight: 361 KB
• Volume: 104
• Category: Article
• ISSN: 1381-1169
• DOI: 10.1016/1381-1169(95)00199-9

✦ Synopsis

The halogenated Porphyrin, 2,12,13,17,l5,~~hy~nat~iron(III) chloride, [ Fe( TPPPBr,)Cl] , catalyzes the oxidation of cyclohexene in the presence of molecular oxygen or iodosobenzene. With PhIO, 77% epoxide is observed, consistent with a mechanism involving a high-valent metaI-oxo species. With dioxygen, however, ahylic alcohol and ketone are observed, suggesting a different mechanism. The relatively high activity of the [Fe( TITPBr,)Cl] /O, system suggests that the reaction involves the formation and decomposition of aIky1 Peroxides.