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 ...
