Liquid phase fluorination of norbornene with 1-chloromethyl-4-fluoro-1,4-diazonia[2.2.2]octane bis(tetrafluoroborate)--F-TEDA resulted in the formation of two rearranged Ritter type products: ...2-exo-acetamido-7-syn-fluoro norbornane and 2-exo-acetamido-7-anti-fluoro norbornane in 1:1 ratio in acetonitrile, while the presence of an external nucleophile, e.g. water or methanol resulted in formation of two additional rearranged products: 2-exo-hydroxy or methoxy -7-syn-fluoro norbornane and 2-exo-hydroxy or methoxy-7-anti-fluoro norbornane. Fluorination of cycloalkenes obeys a simple second order rate equation, relative rates close to unity were found for norbornene/cyclohexene and cyclopentene/cyclohexene pairs. Activation parameters were determined for cycloalkenes in acetonitrile-water (H=14 kcal mol-1 and S=-20 cal mol-1K-1 for norbornene), while the Winstein-Grunwald solvent polarity variation had negligible effect.
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