Abstract
In contrast to limited substitutive fluorination of aromatics with halogen fluorides such as ClF, ClF 3, BrF 3 and IF 5, fluorination is the predominant reaction path with ClF 5. Under non-catalytic liquid phase conditions, benzene was converted to fluorobenzene (54% yield) and chlorobenzene (37% yield), respectively. For a heterocyclic substrate, i.e. 2,4,6-trifluoropyrimidine, substitutive fluorination predominated over chlorination. Three possible fluorination mechanisms are discussed. A transition complex of ClF 5 with benzene is favored. Enhanced exchange fluorination of CCl 4 was effected with ClF 5 (CF 2Cl 2>>CFCl 3>CF 3Cl) as compared with ClF 3 (CFCl 3>>CF 2Cl 2).
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