Iodination of Naphthalenes with Iodine and Sodium Iodate in Aqueous Acetic Acid Medium

Abstract

In the present investigation, iodination of both activated and deactivated naphthalenes has been studied with the iodinating system: I₂NaIO₃H₂SO₄ in aqueous acetic acid medium. Initially, a systematic kinetic study of iodination of aromatics has been carried out with the same system; from the results, the concentrations of the various reagents for effective iodination were fixed and the formation of an electrophilic iodonium species I⁺ which is responsible for the iodination of aromatic nucleus was suggested. The iodination reactions are succeeded by heating the reaction mixture in aqueous acetic acid (AcOH/H₂O 80/20 (v/v)). The identity of the iodinated product of each substrate was established by recording its mass and IR spectral data.