Reaction with antimony dioxide chloride

Few 1-benzothiophene-S-oxides 218 were obtained in moderate yields by treatment of 1-arylacetylenes 219 with sulfur dioxide and benzene in the presence of antimony pentafluoride (equation 127). A series of cyclic sulphoxides have been prepared by hydrolysis of the corresponding alkoxy sulphonium salts 220 " (equation 128). Syn-sulphoxide 221 was obtained in a low yield (15-20%) in the reaction of the dianion of cyclooctatetraene 222 with thionyl chloride (equation 129). 

All of the chemistry described in this Section consists of either simple halide exchange reactions (for the formation of other carbonyl halides) or deoxohalogenation reactions (for the formation of perhalomethanes), with the exceptions of the weak adduct formation observed for antimony(V) chloride and dioxide chloride. 

Moissan and Lebeau (1901) produced sulfuryl fluoride by the combination of sulfur dioxide with fluorine (217). Other processes which have been used to produce the gas are (a) the thermal decomposition of barium fluorosulfonate or certain other fluorosulfonates (188, 221, 808), (b) the reaction of sulfur dioxide with chlorine and hydrogen fluoride in the presence of activated charcoal at 400° (11), (c) the reaction of sulfur dioxide and chlorine with potassium or sodium fluoride at 400° (328), (d) the disproportionation of sulfuryl chlorofluoride at 300-400° (328), (e) the reaction of sulfuryl chloride with a mixture of antimony trifluoride and antimony pentachloride at about 250° (86), (f) the reaction of sulfur dioxide with silver difluoride (86), (g) the reaction of thionyl fluoride with oxygen in an electrical discharge (314), (h) electrolysis of a solution of fluorosulfonic acid in hydrogen fluoride (264), ( ) the reaction of fluorine with sodium sulfate, sodium sulfite or sodium thiosulfate (229, 239), (j) the reaction of hydrogen fluoride with sulfuryl chloride (820). 

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