The reaction of para-PhCB10H10CLi with excess C6F6 produced para-PhCB10H10CC6F5 (52%) and the tetrafluorophenylene bridged system 1,4-(para-PhCB10H10C)2C6F4 (31%). The C-pentafluorophenyl compound para-PhCB10H10CC6F5 afforded good yields of 1,4-tetrafluorophenylene bridged carboranes with suitable nucleophilic reagents: 1-(para-PhCB10H10C)-4-(ortho-HCB10H10C)C6F4 from ortho-HCB10H10CLi, 1-(para-PhCB10H10C)-4-HOC6F4 from KOH and 1-(para-PhCB10H10C)-4-EtOC6F4 from KOEt. Addition of the monolithiated carborane, meta-PhCB10H10CLi, to excess C6F6 produced meta-PhCB10H10CC6F5 (19%) and the two-cage carborane 1,4-(meta-PhCB10H10C)2C6F4 (70%). Reactions of the novel C-pentafluorophenyl meta carborane, meta-PhCB10H10CC6F5, with nucleophiles, ortho-HCB10H10CLi and nBuLi, gave 1-(meta-PhCB10H10C)-4-(ortho-HCB10H10C)C6F4 and 1-(meta-PhCB10H10C)-4-nBuC6F4, respectively. The structure of 1-(para-PhCB10H10C)-4-EtOC6F4 was determined by a single crystal X-ray diffraction study.