Active-sodium-promoted reductive cleavage of halogenated benzoic acids
2010; Elsevier BV; Volume: 66; Issue: 47 Linguagem: Inglês
10.1016/j.tet.2010.09.072
ISSN1464-5416
AutoresUgo Azzena, Giovanna Dettori, Sarah Mocci, Luisa Pisano, Giovanni Cerioni, Francesca Mocci,
Tópico(s)Environmental remediation with nanomaterials
ResumoThe 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.
Referência(s)