Synthetic studies in a tetrafluorotricyclo[5.2.1.0(2,6)] decane series

Tricyclic model alkene (3,3,5,5-tetrafluoro-4-oxa-tricyclo[5.2.1.0(2,6)]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 pi electrons of the double bond. A brief discussion linking steric hindrance in polycyclic alkenes with the presence of fluorine atoms is prov ided. (C) 2000 Elsevier Science S.A. All rights reserved.