Direct Aromatic Periodination

Article abstract of DOI:10.1021/jo00191a003

Periodic acid and iodine in concentrated sulfuric acid exhaustively iodinated unactivated aromatic substrates.Thus benzene, nitrobenzene, benzoic acid, chlorobenzene, phthalic anhydride, and toluene were all converted to their periodo derivatives.Benzonitrile was converted to pentaiodobenzamide.This direct method compared favorably with the only general periodination procedure available, a mercuration/iododemercuration sequence.Partially iodinated products were obtained under less vigorous conditions.Thus, triiodo derivatives were obtained from nitrobenzene, benzo-ic acid, and toluene; tetraiodo derivatives were obtained from benzene, chlorobenzene, and trifluorobenzene.