title: Intermolecular reductive radical addition to 2-(2,2,2-trifluoroethylidene)-1,3-dithiane 1-oxide: experimental and theoretical studies.
abstract: Tin hydride mediated radical addition of organic halide to 2-(2,2,2-trifluoroethylidene)-1,3-dithiane 1-oxide has been devised. The reaction is equivalent to an unrealizable radical addition to trifluoromethylketene, providing useful α-trifluoromethyl carbonyl equivalents. The trifluoromethyl and the sulfoxide groups of the substrate play key roles for the success of the radical addition, lowering the barrier of the radical addition step and controlling the stereoselectivity of the reaction, which DFT calculations have elucidated.
authors.affiliation: Department of Material Chemistry, Graduate School of Engineering, Kyoto University, Kyoto-daigaku Katsura, Nishikyo-ku, Kyoto 615-8510, Japan.
authors.forename: Ryota
authors.initials: R
authors.lastname: Nakayama
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Matsubara
authors.forename: Daishi
authors.initials: D
authors.lastname: Fujino
authors.forename: Takayuki
authors.initials: T
authors.lastname: Kobatake
authors.forename: Suguru
authors.initials: S
authors.lastname: Yoshida
authors.forename: Hideki
authors.initials: H
authors.lastname: Yorimitsu
authors.forename: Koichiro
authors.initials: K
authors.lastname: Oshima
mesh_terms: D005609:Free Radicals / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013457:Sulfur Compounds / Q000737:chemistry*
chemical_list: C541179:2-(2,2,2-trifluoroethylidene)-1,3-dithiane monoxide; D005609:Free Radicals; D006845:Hydrocarbons, Fluorinated; D013457:Sulfur Compounds