title: Easy access to CF2-containing molecules based on the reaction of 2,2,3,3-tetrafluorooxetane with various nucleophiles.
abstract: 2,2,3,3-Tetrafluorooxetane reacted easily with organolithium reagents to give 1,1,3-trisubstituted 2,2-difluoropropan-1-ols in good to excellent yields. On the other hand, the reaction with Grignard reagent led to 3-bromo-1,1-disubstituted 2,2-difluoropropan-1-ols in good yields. On treating with lithium enolates, generated from enol silyl ethers and MeLi/LiBr, the corresponding 1-bromo-2,2-difluoro-3,5-dicarbonyl compounds were obtained in fair to good yields. 3-Iodo-2,2-difluoropropanoate, prepared readily from 2,2,3,3-tetrafluorooxetane and NaI, reacted successfully with various silyl enol ethers in the presence of a radical initiator to provide the corresponding coupling products in good yields.
authors.affiliation: Department of Chemistry and Materials Technology, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto 606-0962, Japan.
authors.forename: Shigeyuki
authors.initials: S
authors.lastname: Yamada
authors.forename: Masahiro
authors.initials: M
authors.lastname: Kato
authors.forename: Yudai
authors.initials: Y
authors.lastname: Komori
authors.forename: Tsutomu
authors.initials: T
authors.lastname: Konno
authors.forename: Takashi
authors.initials: T
authors.lastname: Ishihara
mesh_terms: D004988:Ethers, Cyclic / Q000737:chemistry*; D005461:Fluorine / Q000737:chemistry*; D005466:Fluorocarbons / Q000737:chemistry*; D005609:Free Radicals; D008094:Lithium / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry
chemical_list: D004988:Ethers, Cyclic; D005466:Fluorocarbons; D005609:Free Radicals; D009942:Organometallic Compounds; D005461:Fluorine; D008094:Lithium; C005287:oxetane