The reactions of aromatic compounds with bromine trifluoride(I): hexafluorobenzene and its derivatives
1975; Elsevier BV; Volume: 6; Issue: 4 Linguagem: Inglês
10.1016/s0022-1139(00)85311-7
ISSN1873-3328
AutoresTony W. Bastock, Mike Harley, A. E. PEDLER, J. C. Tatlow,
Tópico(s)Chemical Reactions and Mechanisms
ResumoAbstract The reactions of mixtures of bromine trifluoride and bromine with hexa-, penta- and bromopenta-fluorobenzene, with octafluorotoluene and decafluoro -p-xylene and 2,3,4,5,6-pentafluorotoluene and -anisole have been investigated. The initial products were polyfluorocyclohexa-1,4-dienes, substituent groups being in the 1-position for electron withdrawing and the 3-position for electron donating groups respectively. The dienes then reacted further to add bromine monofluoride across one or both of the diene double bonds to give bromofluorocyclohexene or polybromofluorocyclohexane isomer mixtures. In the absence of added bromine, no reaction occurred with hexafluorobenzene and reaction was less vigorous and complete with pentafluorobenzene and 2,3,4,5,6-pentafluoroanisole. The mechanism of reaction has been discussed in terms of the ionization potential of the aromatic substrates and the formation of radical cations.
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