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Issue 2, 2003
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A study of the oxidation of ethers with the enzyme laccase under mediation by two N–OH–type compounds

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Abstract

The oxidation of ethers of various structure by O2 with two laccase/[double bond splayed left]N–OH systems (i.e., HBT, 1-hydroxybenzotriazole, and HPI, N-hydroxyphthalimide) is described. The process affords carbonylic products in reasonable-to-good yields. The oxidation is carried out by the intermediate [double bond splayed left]N–O˙ species of the mediators, through a radical H-atom abstraction (HAT) route that represents an elaboration of the HAT route followed with benzyl alcohols. Alternative mechanisms have been considered and dismissed. A comparison with a similar oxidation of ethers by the laccase/TEMPO system, reported previously, is made. A clear-cut specialisation of the mediator vs. the substrate emerges, i.e. the laccase/HBT system is more competent for the oxidation of ethers, whereas the laccase/TEMPO system was most proficient in the oxidation of benzyl alcohols.

Graphical abstract: A study of the oxidation of ethers with the enzyme laccase under mediation by two N–OH–type compounds

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Publication details

The article was received on 07 Nov 2002, accepted on 25 Nov 2002 and first published on 13 Dec 2002


Article type: Paper
DOI: 10.1039/B210978F
Citation: New J. Chem., 2003,27, 329-332
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    A study of the oxidation of ethers with the enzyme laccase under mediation by two N–OH–type compounds

    F. d'Acunzo, P. Baiocco and C. Galli, New J. Chem., 2003, 27, 329
    DOI: 10.1039/B210978F

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