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.

Active-sodium-promoted Reductive Cleavage of Halogenated Benzoic Acids / Azzena, Ugo Gavino; G., Dettori; S., Mocci; Pisano, Luisa; G., Cerioni; F., Mocci. - In: TETRAHEDRON. - ISSN 0040-4020. - 66:47(2010), pp. 9171-9174. [10.1016/j.tet.2010.09.072]

Active-sodium-promoted Reductive Cleavage of Halogenated Benzoic Acids

AZZENA, Ugo Gavino;PISANO, Luisa;
2010

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.
File in questo prodotto:
Non ci sono file associati a questo prodotto.

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11388/49655
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 9
  • ???jsp.display-item.citation.isi??? 9
social impact