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Ueber die Reaktion von Chlortrifluorethen mit Schwefeltrioxid
Gille, E.,Hass, D.,Holfter, H.,Schoenherr, M.
, p. 145 - 150 (1994)
Chlorotrifluorethane β-sultone has been synthesized in good yield by bubbling chlorotrifluorethene (CTFE) through liquid sulfur trioxide at atmospheric pressure.By treatment of the sultone with catalytic amounts of triethylamine, quantitative rearrangement to four different fluoroacetylsulfuric acid halides, i.e.F(O)C-CF2-SO2F, F(O)C-CFCl-SO2F, F(O)C-CF2-SO2Cl and F(O)C-CFCl-SO2Cl, occurred.These products were partially separated by fractional distillation.Their concentrations were established from determinations of hydrolyzable halogen and 19F nuclear magnetic resonance spectra.These results confirm that the reaction of CTFE with sulfur trioxide gives approximately equal amounts of the two possible isomeric sultones: which rearrange to fluorodihaloacetylsulfonic acid halides by cyclic mechanism, followed by an F(-)/Cl(-) exchange at the sulfonyl halide groups. - Keywords: Chlorofluorethene; Reaction; Sulfur trioxide; β-Sultone formation; NMR spectroscopy
