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Oxidation of alkanes withm-chloroperbenzoic acid catalyzed by iron(III) chloride and a polydentate amine

Authors
Journal
Journal of Molecular Catalysis A Chemical
1381-1169
Publisher
Elsevier
Publication Date
Volume
219
Issue
2
Identifiers
DOI: 10.1016/j.molcata.2004.05.020
Keywords
  • Alkanes
  • Biomimetics
  • Iron Complexes
  • Ligand Effects
  • Meta-Chloroperbenzoic Acid (Mcpba)

Abstract

Abstract Tetradentate amine N, N′-bis(2-pyridylmethylene)-1,4-diaminodiphenyl ether (compound 1) dramatically accelerates the oxidation of alkanes with MCPBA in acetonitrile catalyzed by FeCl 3, whereas N,N′-bis(2-pyrrolidinmethylene)-1,4-diaminodiphenyl ether ( 2) does not affect the reaction. The selectivity of the reaction in the presence of 1 is noticeably higher than that in its absence. On the basis of the kinetic study and selectivity parameters a mechanism has been proposed which includes the formation of a complex between a molecule of MCPBA and coordinated to ligand 1 iron ion. This complex decomposes to produce a Fe(II) derivative which is further oxidized by MCPBA to generate a ( 1·FeO) 4+ species reacting with both alkane and acetonitrile. Finally, alkyl hydroperoxide is formed which partially decomposes to produce more stable corresponding alcohol and ketone (aldehyde).

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