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Active-sodium-promoted reductive cleavage of halogenated benzoic acids

Azzena, Ugo Gavino and Dettori, Giovanna and Mocci, Sarah and Pisano, Luisa and Cerioni, Giovanni and Mocci, Francesca (2010) Active-sodium-promoted reductive cleavage of halogenated benzoic acids. Tetrahedron, Vol. 66 (47), p. 9171-9174. ISSN 0040-4020. Article.

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DOI: 10.1016/j.tet.2010.09.072

Abstract

The outcome of the reaction between 1,2-diaryl-1,2-disodioethanes and halogenated benzoic acids strongly depends on the nature of both reaction partners. Indeed, whilst chloro-, bromo- and iodobenzoic acids are easily dehalogenated, the reductive cleavage of fluorobenzoic acids proceeds to a high extent only in the presence of the dianions endowed with more powerful reducing properties. Moreover, it was observed that ortho-substituted benzoic acids are more easily dehalogenated than the corresponding para or meta isomers. These observations allowed the development of reaction conditions for the exhaustive or regioselective cleavage of selected polyhalogenated benzoic acids.

Item Type:Article
ID Code:5411
Status:Published
Refereed:Yes
Uncontrolled Keywords:Active sodium, electron transfer, hydrodehalogenation, organic pollutants, reduction, vic-diorganometals
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01 Dipartimenti > Chimica
Publisher:Pergamon / Elsevier
ISSN:0040-4020
Deposited On:03 Feb 2011 08:25

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