SUBSTITUTIVE AROMATIC FLUORINATION WITH CHLORINE PENTAFLUORIDE

DOI: 10.1016/S0022-1139(00)81475-X

Source and publish data:

Journal of Fluorine Chemistry p. 435 - 446 (1984)

Update date:2022-08-12

Topics:

Authors:

Boudakian, Max M.

Hyde, Gene A.

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Article abstract of DOI:10.1016/S0022-1139(00)81475-X

In contrast to limited substitutive fluorination of aromatics with halogen fluorides such as ClF, ClF3, BrF3 and IF5, fluorination is the predominant reaction path with ClF5.Under non-catalytic liquid phase conditions, benzene was converted to fluorobenzene (54percent yield) and chlorobenzene (37percent yield), respectively.For a heterocyclic substrate, i.e. 2,4,6-trifluoropyrimidine, sunstitutive fluorination predominated over chlorination.Three possible fluorination mechanisms are discussed.A transition complex of ClF5 with benzene is favored.Enhanced exchange fluorination of CCl4 was effected with ClF5 (CF2Cl2 >> CFCl3 > CF3Cl) as compared with ClF3 (CFCl3 >> CF2Cl2)

Full text of DOI:10.1016/S0022-1139(00)81475-X

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