title: Preparation, X-ray structure, and reactivity of 2-iodylpyridines: recyclable hypervalent iodine(V) reagents.
abstract: 2-Iodylpyridine and four examples of 3-alkoxy-2-iodylpyridines were prepared by oxidation of the respective 2-iodopyridines with 3,3-dimethyldioxirane. Structures of 2-iodylpyridine, 2-iodyl-3-isopropoxypyridine, and 2-iodyl-3-propoxypyridine were established by single-crystal X-ray diffraction analysis. 2-Iodyl-3-propoxypyridine has moderate solubility in organic solvents (e.g., 1.1 mg/mL in acetonitrile) and can be used as a recyclable reagent for oxidation of sulfides and alcohols. The reduced form of this reagent, 2-iodo-3-propoxypyridine, can be effectively separated from the reaction mixture by treatment with diluted sulfuric acid and recovered from the acidic aqueous solution by adding aqueous sodium hydroxide.
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.forename: Christopher T
authors.initials: CT
authors.lastname: Banek
authors.forename: Mekhman S
authors.initials: MS
authors.lastname: Yusubov
authors.forename: Victor N
authors.initials: VN
authors.lastname: Nemykin
authors.forename: Viktor V
authors.initials: VV
authors.lastname: Zhdankin
mesh_terms: D000438:Alcohols / Q000737:chemistry; D018360:Crystallography, X-Ray; D007202:Indicators and Reagents / Q000737:chemistry; D007455:Iodine / Q000737:chemistry*; D010084:Oxidation-Reduction; D011725:Pyridines / Q000138:chemical synthesis / Q000737:chemistry*; D013440:Sulfides / Q000737:chemistry
chemical_list: D000438:Alcohols; D007202:Indicators and Reagents; D011725:Pyridines; D013440:Sulfides; D007455:Iodine