title: [Synthesis and reaction of hypervalent λ3-iodane-crown ether complexes].
abstract: In this review, we show that intermolecular hypervalent I(III)…O interactions play an essential role in the complexation of organo-λ(3)-iodanes with crown ethers. In addition to the well-known driving force for the complexation of crown ethers, ion-dipole interaction, and hydrogen bonding interaction, our result provides a new class of interaction in supramolecular chemistry of crown ethers. Both solid state structure analysis and solution chemistry indicate that diaryl-, 1-alkenyl(phenyl)-, 1-alkynyl(phenyl)-, and hydroxy(phenyl)-λ(3)-iodanes form stable complexes with 18-crown-6 through hypervalent I(III)…O interactions. The complexation not only increases the stability of these hypervalent λ(3)-iodanes but also holds its high reactivity toward nucleophiles. The complex of hydroxy(phenyl)-λ(3)-iodanes with 18-crown-6 serve as versatile oxidizing agents, especially in water.
authors.affiliation: Department of Pharmaceutical Organic Chemistry, Institute of Health Biosciences, Graduate School of the University of Tokushima, Tokushima, Japan. kmiya@ph.tokushima-u.ac.jp
authors.forename: Kazunori
authors.initials: K
authors.lastname: Miyamoto
mesh_terms: D043844:Crown Ethers / Q000138:chemical synthesis* / Q000737:chemistry*; D004355:Drug Stability; D006860:Hydrogen Bonding; D046911:Macromolecular Substances; D016877:Oxidants; D014867:Water
chemical_list: D043844:Crown Ethers; D046911:Macromolecular Substances; D016877:Oxidants; D014867:Water; C015762:18-crown-6