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Selectivity enhancement of aromatic halogenation reactions at the micellar interface: effect of highly ionic media

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Abstract

Halogenation (iodination and bromination) of various aromatic compounds has been studied in micellar media in order to observe the effect on regioselectivity and conversion of the reaction. The addition of surfactant causes a change in the chemical shifts of the aromatic proton resonance of phenol which proves the orientation of the aromatic compound on the micellar surface. However, increase in ionic strength of the reaction media affects the selectivity of reaction by disturbing this spatial orientation of the aromatic compound in the micelle. Selectivity towards particular isomers is dependent on the concentration of the surfactant. In bromination of chlorobenzene (deactivated aromatic compound) enhancement in selectivity and conversion towards the para isomer has been observed.

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Acknowledgments

We are grateful to Rhodes University Joint Research Committee (JRC) for providing financial support for this work (Rhodes University JRC grant number 35047).

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Authors and Affiliations

  1. Natural Product and Medicinal Chemistry (NPMC) Research Group, Division of Pharmaceutical Chemistry, Faculty of Pharmacy, Rhodes University, Grahamstown, 6140, South Africa

    Bhupesh S. Samant

  2. Department of Chemical Engineering, Institute of Chemical Technology, Matunga, Mumbai, 400019, India

    Sunil S. Bhagwat

Authors
  1. Bhupesh S. Samant
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  2. Sunil S. Bhagwat
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Corresponding author

Correspondence to Bhupesh S. Samant.

Electronic supplementary material

Below is the link to the electronic supplementary material, which includes 1H NMR spectra for the solubilization study of phenol.

Supplementary material 1 (DOCX 294 kb)

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Samant, B.S., Bhagwat, S.S. Selectivity enhancement of aromatic halogenation reactions at the micellar interface: effect of highly ionic media. Monatsh Chem 143, 1039–1044 (2012). https://doi.org/10.1007/s00706-011-0677-1

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  • DOI: https://doi.org/10.1007/s00706-011-0677-1

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