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Issue 35, 2013
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A new method for the nitrosation of 1,3-diketones applied to 3-ethyl- and 3-methyl pentane-2,4-dione

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Abstract

The nitrosation of 3-ethylpentane-2,4-dione (EPD) and 3-methylpentane-2,4-dione (MPD) has been performed in aqueous acid medium following a new procedure for sample preparation. The two reagents, diketone and sodium nitrite, were mixed together in alkaline medium to give the corresponding enolate (E) and nitrite ion (NO2). The enol nitrosation reaction starts after acidifying the reaction medium. Different experimental conditions were tested in order to adapt the reaction time scale to conventional or stopped-flow UV-vis spectrophotometry. The objectives of this study were to demonstrate that the decomposition of nitrous acid is negligible in the time scale of the nitrosation reaction and to corroborate the published reaction mechanism for the nitrosation of some 3-substituted diketones that it was assumed to proceed through a chelate nitrosyl intermediate. The results were compared with that obtained when the last reagent, normally the ketone, was added over an acid mixture of the rest of the reactants, that is, the protocol followed in previously published studies.

Graphical abstract: A new method for the nitrosation of 1,3-diketones applied to 3-ethyl- and 3-methyl pentane-2,4-dione

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Publication details

The article was received on 21 May 2013, accepted on 11 Jun 2013 and first published on 17 Jun 2013


Article type: Paper
DOI: 10.1039/C3RA42508H
RSC Adv., 2013,3, 15192-15201

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    A new method for the nitrosation of 1,3-diketones applied to 3-ethyl- and 3-methyl pentane-2,4-dione

    E. Iglesias, RSC Adv., 2013, 3, 15192
    DOI: 10.1039/C3RA42508H

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