Evaluation of the reactivity and regioselectivity of superelectrophilic iodinating systems

V. K. Chaikovskii, V. D. Filimonov, A. A. Funk

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Iodination of o-nitrotoluene in H2SO4 or CF 3SO3H at 0°C with compounds having a nitrogen-iodine bond leads to the formation of isomeric mono- and diiodo derivatives whose ratio differs from the statistical value. The reaction of nitrobenzene with 2 equiv of N-I reagents in trifluoromethanesulfonic acid at 0°C takes less than 1 min and yields 79-85% of m-iodonitrobenzene. The electrophilic reactivity of the iodinating agents was estimated by quantum-chemical methods.

Original languageEnglish
Pages (from-to)1349-1352
Number of pages4
JournalRussian Journal of Organic Chemistry
Issue number9
Publication statusPublished - Sep 2009


ASJC Scopus subject areas

  • Organic Chemistry

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