A novel bulky aryllithium, 2,6-bis{2,5-bis[bis(trimethylsilyl)methyl]phenyl}phenyllithium (BbspLi), was synthesized. Reactions of BbspLi 5 with Group 14 electrophiles, such as stannous chloride, with carbon tetrachloride or tetrachlorometallanes gave fluorene 6. Reaction of BbspLi with carbon tetrachloride gave benzyl chloride 8, which converted to 6 under acidic conditions. BbspLi 5 isomerized to the corresponding benzyl anion 10, which underwent halophilic reactions with Group 14 electrophiles to give fluorene 6 via the benzyl chloride intermediate 8.