Active-sodium-promoted reductive cleavage of halogenated benzoic acids |
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Authors: | Ugo Azzena Giovanna Dettori Luisa Pisano Francesca Mocci |
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Affiliation: | a Dipartimento di Chimica, Università di Sassari, via Vienna 2, I—07100 Sassari, Italy b Dipartimento di Scienze Chimiche, Università di Cagliari, Complesso Universitario, S.S. 554 bivio per Sestu, I—09042 Monserrato (Ca), Italy |
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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. |
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Keywords: | Active sodium Electron transfer Hydrodehalogenation Organic pollutants Reduction vic-Diorganometals |
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