Iron porphyrins-catalysed oxidation of α-alkyl substituted mono and dimethoxylated benzyl alcohols

• Authors: Claudia Fabbri , Claudia Aurisicchio , Osvaldo Lanzalunga
• Languages of publication: EN

Abstracts

EN

The mechanisms of oxidation of a series of a-alkyl substituted mono and dimethoxylated benzyl alcohols catalysed by mesotetrakis(4-N-methylpyridynium)porphyrin iron (III) chloride (FeTMPyPCl) and meso-tetrakis(4-sulfonatophenyl)porphyrin iron (III) chloride (FeTSPPCl) in aqueous solution with KHSO5 as oxygen atom donor and by meso-tetrakis(pentafluorophenyl)-porphyrin iron (III) chloride (FeTPFPPCl) in dichloromethane employing iodosylbenzene as oxidant have been investigated. In the highly polar aqueous medium an electron transfer mechanism is operating. With FeTMPyPCl, which is a much more efficient catalyst than FeTSPPCl due to the presence of stronger electron withdrawing substituents, formation of side-chain oxidation products accompanies generation of nuclear oxidation products. In the low polar solvent dichloromethane, two competing mechanism have been suggested: hydrogen atom transfer and formation of a complex between the active species iron-oxo porphyrin radical cation and the substrate. [...]

Keywords

EN

Iron porphyrins; Oxidation

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2008
• Volume: 6
• Issue: 2
• Pages: 145-153

Dates

published

1 - 6 - 2008

online

17 - 4 - 2008

Contributors

author

Claudia Fabbri

• Dipartimento di Chimica, Sapienza Università di Roma and Istituto CNR di Metodologie Chimiche (IMC-CNR), Sezione Meccanismi di Reazione, P.le Aldo Moro 5, 00185, Rome, Italy

author

Claudia Aurisicchio

• Dipartimento di Chimica, Sapienza Università di Roma and Istituto CNR di Metodologie Chimiche (IMC-CNR), Sezione Meccanismi di Reazione, P.le Aldo Moro 5, 00185, Rome, Italy

author

Osvaldo Lanzalunga

• Dipartimento di Chimica, Sapienza Università di Roma and Istituto CNR di Metodologie Chimiche (IMC-CNR), Sezione Meccanismi di Reazione, P.le Aldo Moro 5, 00185, Rome, Italy

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Identifiers

DOI

10.2478/s11532-008-0005-8