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

✍ Scribed by Georgiy B Shul’pin; Helen Stoeckli-Evans; Dalmo Mandelli; Yuriy N Kozlov; Ana Tesouro Vallina; Camile B Woitiski; Ricardo S Jimenez; Wagner A Carvalho

Publisher: Elsevier Science
Year: 2004
Tongue: English
Weight: 187 KB
Volume: 219
Category: Article
ISSN: 1381-1169
DOI: 10.1016/j.molcata.2004.05.020

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✦ Synopsis

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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