Reaction of fluoroxysulfate with aromatic compounds

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. Prod...

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Veröffentlicht in:	J. Am. Chem. Soc.; (United States) 1981-04, Vol.103 (8), p.1964-1968
Hauptverfasser:	Ip, Dominic P, Arthur, Carol D, Winans, Randall E, Appelman, Evan H
Format:	Artikel
Sprache:	eng
Schlagworte:	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 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY 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
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Beschreibung
Zusammenfassung:	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.
ISSN:	0002-7863 1520-5126
DOI:	10.1021/ja00398a015