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 pare or meta isomers These observations allowed the development of reaction conditions for the exhaustive or regioselective cleavage of selected polyhalogenated benzoic acids (C) 2010 Elsevier Ltd All rights reserved
Active-sodium-promoted reductive cleavage of halogenated benzoic acids
CERIONI, GIOVANNI;MOCCI, FRANCESCA
2010-01-01
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 pare or meta isomers These observations allowed the development of reaction conditions for the exhaustive or regioselective cleavage of selected polyhalogenated benzoic acids (C) 2010 Elsevier Ltd All rights reserved
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