title: Preparation and X-ray Structural Study of Dibenziodolium Derivatives.
abstract: New experimental procedures for the preparation of dibenziodolium salts by oxidative cyclization of 2-iodobiphenyl in the presence of appropriate strong acids are described. Particularly useful is a convenient one-pot synthesis of dibenziodolium hydrogen sulfate from 2-iodobiphenyl using Oxone as an inexpensive and environmentally safe oxidant. Dibenziodolium hydrogen sulfate, bis(triflyl)imidate, or triflate can be readily converted to various other dibenziodolium derivatives (chloride, bromide, thiocyanate, azide, cyanide, phenylsulfinate) by anion exchange. Structures of key products have been established by single-crystal X-ray diffraction analysis. Particularly interesting is the X-ray structure of dibenziodolium thiocyanate, which represents the first example of a structurally characterized hypervalent iodine compound with a relatively short iodine-sulfur secondary bond distance.
authors.affiliation: ‡The Tomsk Polytechnic University, 634050 Tomsk, Russia.
authors.forename: Pavel S
authors.initials: PS
authors.lastname: Postnikov
authors.affiliation: ‡The Tomsk Polytechnic University, 634050 Tomsk, Russia.
authors.forename: Olga A
authors.initials: OA
authors.lastname: Guselnikova
authors.affiliation: ‡The Tomsk Polytechnic University, 634050 Tomsk, Russia.|§The Siberian State Medical University 634050 Tomsk, Russia.
authors.forename: Mekhman S
authors.initials: MS
authors.lastname: Yusubov
authors.affiliation: †Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, United States.
authors.forename: Akira
authors.initials: A
authors.lastname: Yoshimura
authors.affiliation: †Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, United States.
authors.forename: Victor N
authors.initials: VN
authors.lastname: Nemykin
authors.affiliation: †Department of Chemistry and Biochemistry, University of Minnesota Duluth, Duluth, Minnesota 55812, United States.
authors.forename: Viktor V
authors.initials: VV
authors.lastname: Zhdankin
mesh_terms: D018360:Crystallography, X-Ray; D007455:Iodine / Q000737:chemistry*; D009861:Onium Compounds / Q000737:chemistry*; D010084:Oxidation-Reduction; D013861:Thiocyanates / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D009861:Onium Compounds; D013861:Thiocyanates; C007517:diphenyleneiodonium; D007455:Iodine; C031760:thiocyanate