Synthetic studies in a tetrafluorotricyclo[5.2.1.02,6]decane series

Tricyclic model alkene (3,3,5,5-tetrafluoro-4-oxa-tricyclo[5.2.1.02,6]dec-8-ene (1)) was obtained in a short two-step procedure involving the use of sulfur tetrafluoride as a fluorinating agent. Addition of electrophiles to unhindered exo face of the CC bond occurs easily, and thus, precludes the possibility of deactivating electronic interaction between fluorine atoms and the π electrons of the double bond. A brief discussion linking steric hindrance in polycyclic alkenes with the presence of fluorine atoms is provided.