Abstract
Six chlorofluoropropionyl fluorides were synthesized by converting a −CCl 3 group in perhalogenated chlorofluoropropanes to a −COF group in two reaction steps. The ionic telomerization of the acyl fluorides with hexafluoropropene oxide, catalyzed by fluoride ion, afforded mainly a mixture of 1:1 to 1:3 telomers. In some cases, substitution of chlorine for fluorine in the acyl moiety and hexafluoropropene oxide oligomerization occurred as side reactions. The effect of the number of chlorines in the starting acyl fluoride on the telomer distributions and by product formation is discussed. The reactivity order of the acyl fluorides YCOF in the telomerization reaction was: CF 3CClF ( 2a ), CClF 2CF 2 ( 2b ) > CF 3CCl 2 ( 3a ), CClF 2CClF ( 3b ) > CClF 2CCl 2 ( 4a ), CCl 2FCClF ( 4b ). Possible reaction pathways are discussed.
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