Evaluation of the reactivity and regioselectivity of superelectrophilic iodinating systems

VK Chaikovskii, VD Filimonov, AA Funk

Index: Chaikovskii; Filimonov; Funk Russian Journal of Organic Chemistry, 2009 , vol. 45, # 9 p. 1349 - 1352

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Citation Number: 3

Abstract

Abstract Iodination of o-nitrotoluene in H 2 SO 4 or CF 3 SO 3 H 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 NI 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 ...