Abstract
1-Azabicyclo[5.3.0]decane-5,10-dione has been prepared and fluorinated using sulfur tetrafluoride at different temperatures. Whereas the carbonyl ketone was fluorinated at room temperature, the amidic CN bond remained essentially untouched even at 160 °C for 24 h. The resulting difluorobicyclic lactam was reduced to the corresponding bicyclic tertiary amine which proved to be more stable than the hydrocarbon analog.
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