Evaluation of the reactivity and regioselectivity of superelectrophilic iodinating systems
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.
Iodination of nitroarenes by a superactive reagent based on iodine chloride
Iodine chloride reacts with Ag2SO4 in H2SO4 to give a new superelectrophilic reagent capable of iodinating nitrobenzene, halogenated nitrobenzenes, nitrotoluenes, and aromatic compounds with two nitro groups in the ring. Mononitroarenes are easily iodinated at 0-20 deg C, while dinitroarenes require heating to 100-170 deg C.
Chaikovskii, V. K.,Kharlova, T. S.,Filimonov, V. D.
p. 1291 - 1294
(2007/10/03)
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