Reaction of fluoroxysulfate with aromatic compounds

Journal Article · Wed Apr 22 04:00:00 EST 1981 · J. Am. Chem. Soc.; (United States)

DOI:https://doi.org/10.1021/ja00398a015· OSTI ID:6342076

Ip, D P; Arthur, C D; Winans, R E; Appelman, E H

The fluoroxysulfate ion, SO/sub 4/F/sup -/, substitutes fluorine on aromatic compounds in acetonitrile solution at room temperature. However, benzyl fluoride is the principal product from toluene. Other products are also formed, particularly in the case of the less reactive aromatic substrates. Product distributions and relative reactivities are interpreted in terms of an initial electrophilic attack that can be followed by free-radical side reactions.

• Research Organization: Argonne National Lab., IL
• OSTI ID: 6342076
• Journal Information: J. Am. Chem. Soc.; (United States), Journal Name: J. Am. Chem. Soc.; (United States) Vol. 103:8; ISSN JACSA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALKALI METAL COMPOUNDS
ANIONS
ANISOLE
AROMATICS
BENZENE
BIPHENYL
CESIUM COMPOUNDS
CHARGED PARTICLES
CHEMICAL REACTIONS
CONDENSED AROMATICS
ETHERS
FLUORINATED AROMATIC HYDROCARBONS
FLUORINE COMPOUNDS
HALOGEN COMPOUNDS
HALOGENATED AROMATIC HYDROCARBONS
HYDROCARBONS
HYDROXY COMPOUNDS
IONS
NAPHTHALENE
NITRILES
NITRO COMPOUNDS
NITROBENZENE
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXYGEN COMPOUNDS
PHENOL
PHENOLS
RUBIDIUM COMPOUNDS
SULFUR COMPOUNDS
TOLUENE