Abstract
Halofluorination of norbornadiene with N-bromosuccinimide, N-chlorosuccinimide or xenon difluoride in the presence of polyhydrogen fluoride-pyridine resulted in the formation of three products: 3- endo-halo-5- exo-fluoro ( 2) and 3- exo-halo-5- exo-fluoronortricyclane ( 3), and 2- exo-fiuoro-7- syn-halo-norbornene-5 ( 4). The exo-attack of the electrophile on norbornadiene is slightly predominant (65% X = Br, 64% X = Cl, 73% X = F) over the endo-attack. The Meerwein-Wagner rearrangement occurred only in the case of chlorine or fluorine halosubstituents of β-carbonium ions formed by exo attack of the electrophile.
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