title: Electrophilic monoiodination of terminal alkenes.
abstract: An excess of elemental iodine in N,N-dimethylacetamide enables effective 3/iodanylium-de-hydronation of terminal alkenes with 3-iodopropene derivatives and hydrogen iodide formation within minutes at room temperature. The optimal molar ratio of iodine to substrate was decreased to 1 : 1 when hydrogen iodide formed was oxidized on a platinum anode. The electrolytic oxidation recovers iodine as a reagent and diminishes the hydrogen iodide inhibitory action to accomplish the monoiodination. The proposed reaction mechanism is based on kinetic measurements and quantum mechanics calculations.
authors.affiliation: University of Minnesota, Natural Resources Research Institute, 5013 Miller Trunk Highway, Duluth, MN 55811, USA.
authors.forename: Sergiy V
authors.initials: SV
authors.lastname: Yemets
authors.forename: Tatyana E
authors.initials: TE
authors.lastname: Shubina
authors.forename: Pavel A
authors.initials: PA
authors.lastname: Krasutsky
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry*; D007700:Kinetics; D008958:Models, Molecular; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D011789:Quantum Theory
chemical_list: D000475:Alkenes