Journal of the American Chemical Society p. 4357 - 4363 (1989)
Update date:2022-08-11
Topics:
Arasasingham, Ramesh D.
Balch, Alan L.
Cornman, Charles R.
Latos-Grazynski, Lechoslaw
The behavior of PFeIIICHR2 (P is a porphyrin dianion) in solution especially in the presence of dioxygen has been examined by (1)H and (2)H NMR measurements.Evidence for the photolytic Fe-C bond homolysis with the formation of PFeII is presented.Addition of dioxygen to PFeCH2R produces two unstable intermediates, PFeIIIO2CH2R and PFeIIIOH, which may be directly observed at low temperatures.These form and decompose through the following reactions: PFeIIICH2R + O2 -> PFeIIIO2CHR2; PFeIIIO2CHR2 -> PFeIIIOH + O=CR2; 2PFeIIIOH -> PFeIIIOFeIIIP + H2O.The formation of the product aldehyde or ketone has been established for methyl, ethyl, isopropyl, n-propyl, and benzyl ligands axially coordinating iron.The dioxygen insertion is retarded by the coordination of N-methylimidazole to the sixth iron coordination site or by employing a sterically encumbered porphyrin.PFeIIIOH catalyzes the decomposition of ethyl hydroperoxide to give acetaldehyde as the major organic product.
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