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On the Mechanism of Epoxidation and Hydroxylation Catalyzed by Iron Porphyrins. Evidence for Non-Intersecting Reaction Pathways

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Bioinorganic Chemistry

Part of the book series: NATO ASI Series ((ASIC,volume 459))

Abstract

The oxygenation of cyclohexene to cyclohexene oxide and cyclohexen-3-ol by (O)FeIV TMP+(X) (1) at various temperatures was compared with the iodosylbenzene mediated reaction catalyzed by chloro-5,10,15,20-tetramesitylporphyrinatoiron(III) [FeIII(TMP)Cl]. The product ratios were found to depend on the axial ligand X in 1 and on the temperature in an unusual way. The results demonstrate that at least one reaction intermediate must be produced and further, that while the epoxidation proceeds via the formation of a complex between 1 and the olefin, the hydroxylation reaction proceeds by a non-intersecting reaction pathway not involving this complex.

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Authors and Affiliations

  1. Department of Chemistry, Princeton University, Princeton, New Jersey, 08544, USA

    John T. Groves & Zeev Gross

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  1. John T. Groves
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  2. Zeev Gross
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Editors and Affiliations

  1. Department of General and Inorganic Chemistry, Aristotle University of Thessaloniki, Thessaloniki, 54006, Greece

    Dimitris P. Kessissoglou

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© 1995 Springer Science+Business Media Dordrecht

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Groves, J.T., Gross, Z. (1995). On the Mechanism of Epoxidation and Hydroxylation Catalyzed by Iron Porphyrins. Evidence for Non-Intersecting Reaction Pathways. In: Kessissoglou, D.P. (eds) Bioinorganic Chemistry. NATO ASI Series, vol 459. Springer, Dordrecht. https://doi.org/10.1007/978-94-011-0255-1_4

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  • DOI: https://doi.org/10.1007/978-94-011-0255-1_4

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-94-010-4113-3

  • Online ISBN: 978-94-011-0255-1

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