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Active-alkali metal-promoted reductive cleavage of chlorinated phenols

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Abstract

We investigated the degradation of chlorinated phenols under reductive electron transfer reaction conditions. Although Li and Na metal proved useless, activated forms of these metals, either their soluble naphthalene radical anions or 1,2-diarylethane dianions, promoted the degradation of the starting materials to various extents. Additionally, efficient dehalogenation of the sodium salts of several mono-, di-, and tri-chlorophenols was obtained by their reduction with an excess of Na metal and a catalytic amount of naphthalene.

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Acknowledgments

Financial support from the Università di Sassari (Fondo di Ateneo per la Ricerca) is gratefully acknowledged. G.D. acknowledges financial support from the Regione Autonoma della Sardegna (Italy), through the project “Master and Back-Percorsi di rientro;” M.P. acknowledges financial support from the Regione Autonoma della Sardegna (Italy), through the project “Promozione della Ricerca Scientifica e dell’Innovazione Tecnologica in Sardegna.”

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Authors and Affiliations

  1. Dipartimento di Chimica, Università di Sassari, via Vienna 2, 07100, Sassari, Italy

    Ugo Azzena, Giovanna Dettori, Luisa Pisano & Mario Pittalis

  2. Dipartimento di Scienze del Farmaco, Università di Sassari, via Muroni, 23/A, 07100, Sassari, Italy

    Giuseppe Mangano, Giacomo Petretto & Giorgio Pintore

Authors
  1. Ugo Azzena
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  2. Giovanna Dettori
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  3. Luisa Pisano
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  4. Mario Pittalis
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  5. Giuseppe Mangano
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  6. Giacomo Petretto
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  7. Giorgio Pintore
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Correspondence to Ugo Azzena.

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Azzena, U., Dettori, G., Pisano, L. et al. Active-alkali metal-promoted reductive cleavage of chlorinated phenols. Monatsh Chem 143, 601–605 (2012). https://doi.org/10.1007/s00706-012-0726-4

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  • DOI: https://doi.org/10.1007/s00706-012-0726-4

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