2-Iodylphenol Ethers:  Preparation, X-ray Crystal Structure, and Reactivity of New Hypervalent Iodine(V) Oxidizing Reagents

2-Iodylphenol ethers were prepared by the dimethyldioxirane oxidation of the corresponding 2-iodophenol ethers and isolated as chemically stable, microcrystalline products. Single-crystal X-ray diffraction analysis of 1-iodyl-2-isopropoxybenzene <b>8c</b> and 1-iodyl-2-butoxybenzene <b>8d</b> revealed pseudopolymeric arrangements in the solid state formed by intermolecular interactions between IO<sub>2</sub> groups of different molecules. 2-Iodylphenol ethers can selectively oxidize sulfides to sulfoxides and alcohols to the respective aldehydes or ketones.