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• W1966207720 endingPage "2285" @default.
• W1966207720 startingPage "2278" @default.
• W1966207720 abstract "We have recently proposed a mechanism for the epoxidation of cyclooctene by H2O2 catalyzed by iron(III) [tetrakis(pentafluorophenyl)]porphyrin chloride, (F20TPP)FeCl, in solvent containing methanol [Stephenson, N. A.; Bell, A.T. Inorg. Chem. 2006, 45, 2758−2766]. In that study, we found that catalysis did not occur unless (F20TPP)FeCl first dissociated, a process facilitated by the solvation of the Cl- anion by methanol and the coordination of methanol to the (F20TPP)Fe+ cation. Methanol as well as other alcohols was also found to facilitate the heterolytic cleavage of the O−O bond of H2O2 coordinated to the (F20TPP)Fe+ cation via a generalized acid mechanism. In the present study, we have shown that catalytic activity of the (F20TPP)Fe+ cation can be achieved in aprotic solvent by displacing the tightly bound chloride anion with a weakly bound triflate anion. By working in an aprotic solvent, acetonitrile, it was possible to determine the rate of heterolytic O−O bond cleavage in coordinated H2O2 unaffected by the interaction of the peroxide with methanol. A mechanism is proposed for this system and is shown to be valid over a range of reaction conditions. The mechanisms for cyclooctene epoxidation and H2O2 decomposition for the aprotic and protic solvent systems are similar with the only difference being the mechanism of proton-transfer prior to heterolytic cleavage of the oxygen−oxygen bond of coordinated hydrogen peroxide. Comparison of the rate parameters indicates that the utilization of hydrogen peroxide for cyclooctene epoxidation is higher in a protic solvent than in an aprotic solvent and results in a smaller extent of porphyrin degradation due to free radical attack. It was also shown that water can coordinate to the iron porphyrin cation in aprotic systems resulting in catalyst deactivation; this effect was not observed when methanol was present, since methanol was found to displace all of the coordinated water." @default.
• W1966207720 created "2016-06-24" @default.
• W1966207720 creator A5017047794 @default.
• W1966207720 creator A5087957929 @default.
• W1966207720 date "2007-02-21" @default.
• W1966207720 modified "2023-10-18" @default.
• W1966207720 title "Mechanistic Study of Iron(III) [Tetrakis(pentafluorophenyl)Porphyrin Triflate (F₂₀TPP)Fe(OTf) Catalyzed Cyclooctene Epoxidation by Hydrogen Peroxide" @default.
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• W1966207720 doi "https://doi.org/10.1021/ic060757c" @default.
• W1966207720 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/17311372" @default.
• W1966207720 hasPublicationYear "2007" @default.
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