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Issue 2, 2014
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Dual role of 2-tosylaminomethylaniline as a ligand and a nucleophile in the copper-mediated oxidation of methanol

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Abstract

Some reactivity in the oxidation of methanol to formaldehyde has been spectroscopically detected on the methanolic mother liquors of a copper(II) complex of a Schiff base ligand derived from the condensation of 8-hydroxyquinoline-2-carboxaldehyde and 2-tosylaminomethylaniline. An investigation has shown that 2-tosylaminomethylaniline (HATS) plays a dual role in the oxidative process acting as a N-donor ligand and reacting in situ with formaldehyde, which leads to 3-tosyl-1,2,3,4-tetrahydroquinazoline (1). This was characterized by using both spectroscopic and X-ray diffraction techniques. The influence of 8-hydroxyquinoline derivatives, water and ligand stoichiometry on the yield of 1 was studied.

Graphical abstract: Dual role of 2-tosylaminomethylaniline as a ligand and a nucleophile in the copper-mediated oxidation of methanol

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Publication details

The article was received on 06 Sep 2013, accepted on 29 Sep 2013 and first published on 02 Oct 2013


Article type: Paper
DOI: 10.1039/C3DT52460D
Citation: Dalton Trans., 2014,43, 722-728
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    Dual role of 2-tosylaminomethylaniline as a ligand and a nucleophile in the copper-mediated oxidation of methanol

    J. Sanmartín-Matalobos, A. M. García-Deibe, L. Briones-Miguéns, C. González-Bello, C. Portela-García and M. Fondo, Dalton Trans., 2014, 43, 722
    DOI: 10.1039/C3DT52460D

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