Abstract
The regioselective oxychlorination of various activated and deactivated aromatic compounds in micellar media was studied. Favourable orientation of substituted aromatic compounds in micelles increased the selectivity toward ortho- chlorination. The selectivity toward ortho- product increased with the increasing order of micellar solubility of activated aromatic compounds from meta- and ortho- cresol to 3,5-xylenol. Significant enhancement toward ortho- selectivity and increase in the percentage conversion in chlorination of deactivated aromatic compounds were observed. Amongst deactivated aromatic compounds studied, benzoic acid, chlorobenzene and iodobenzene showed enhancement in the percentage conversion and selectivity toward ortho- product. The study of proton NMR spectra of aromatic compounds (3,5-xylenol and benzoic acid) in micellar media proved the spatial orientation of these aromatics at micellar interface and explained the mechanism of selectivity enhancement. ortho- selectivity in chlorination was also found to be dependent on the concentration of surfactant employed.
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