Evaluation of the reactivity and regioselectivity of superelectrophilic iodinating systems

Abstract

Iodination of o-nitrotoluene in H2SO4 or CF3SO3H 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.