Cation radicals as intermediates in aromatic halogenation with iodine monochloride: solvent and salt effects on the competition between chlorination and iodination

SM Hubig, W Jung, JK Kochi

Index: Hubig, S. M.; Jung, W.; Kochi, J. K. Journal of Organic Chemistry, 1994 , vol. 59, # 21 p. 6233 - 6244

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Citation Number: 102

Abstract

Three distinct classes of substitutional reactivity can be discerned in the halogenation of a series of methyl-substituted methoxybenzenes (ArH) with iodine monochloride (ICl), namely, exclusive iodination, exclusive chlorination, and mixed iodinatiodchlorination. Spectral studies establish the prior formation of the charge-transfer complex [ArH, ICll which suffers electron transfer to afford the reactive triad [ArH+, I', C1-I according to Scheme 1. Separate ...