In an ongoing project involving the synthesis of functionalized poly(arylene ether)s that carry pendant phenyl sulfonyl groups, the introduction of an iodo group was desired.  The effects of fluorine position on the electrophilic iodination of the 2,4-, 2,6- and 3,5-isomers of difluorodiphenylsulfone were studied.  The relative reactivity, toward EAS, was probed via 13C NMR spectroscopy and verified experimentally by iodination with N-iodosuccinimide.  The product mixtures and corresponding structures indicated that intermediate stability did not always correlate to reactivity.

Effect of fluorine position on the electrophilic halogenation of difluorodiphenyl sulfone isomers

245th National Meeting (2013)

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