An Investigation Into Polyiodination of Activated Benzene Derivatives with Electrophilic Aromatic Substitution Reactions

Gilbert, Dakota (2014) An Investigation Into Polyiodination of Activated Benzene Derivatives with Electrophilic Aromatic Substitution Reactions. Undergraduate thesis, under the direction of Dr. Daniell Mattern from Chemistry and Biochemistry, University of Mississippi.

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Abstract

The aim of this research is to investigate the periodination of benzene derivatives that are activated towards electrophilic aromatic substitution. In this research, a successful electrophilic aromatic substitution reaction was completed with procedures that used iodine with silver sulfate as an activating agent in the reaction mixture. The ball-milling technique with N-iodosuccinnimide as the iodinating reagent was also explored. Only one iodine was added onto 4-iodoanisole as the activated benzene derivative. When 2,4-dichloroanisole was the substrate, a small amount of diiodo product accompanied the monoiodo product, but no triiodo (periodinated) product was observed. Nonetheless, the trials of this research give valuable insight into extensions of previously published works that will not facilitate the polyiodination of activated benzene derivatives.

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