title: Oxidation of primary aliphatic and aromatic aldehydes with difluoro(aryl)-λ3-bromane.
abstract: Oxidation of primary aliphatic aldehydes with p-trifluoromethylphenyl(difluoro)-λ(3)-bromane in dichloromethane at 0 °C afforded acid fluorides selectively in good yields, while that of aromatic aldehydes in chloroform at room temperature produced aryl difluoromethyl ethers. A larger migratory aptitude of aryl groups compared to primary alkyl groups during a 1,2-shift from carbon to an electron-deficient oxygen atom in bromane(III) Criegee-type intermediates will result in these differences in the reaction courses.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokushima, 1-78 Shomachi, Tokushima 770-8505, Japan. mochiai@ph.tokushima-u.ac.jp
authors.forename: Masahito
authors.initials: M
authors.lastname: Ochiai
authors.forename: Akira
authors.initials: A
authors.lastname: Yoshimura
authors.forename: Md Mahbubul
authors.initials: MM
authors.lastname: Hoque
authors.forename: Takuji
authors.initials: T
authors.lastname: Okubo
authors.forename: Motomichi
authors.initials: M
authors.lastname: Saito
authors.forename: Kazunori
authors.initials: K
authors.lastname: Miyamoto
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
chemical_list: D000447:Aldehydes; D006842:Hydrocarbons, Brominated; D006845:Hydrocarbons, Fluorinated