A 300 ml two-necked flask equipped with a magnetic stirrer, a three-way cock and a dropping funnel, was purged thoroughly with nitrogen. Into the flask, octamethyloctahydrodibenzofluorene 2.01 g (5.21 mmol) and dehydrated tetrahydrofuran 40 ml were introduced. With cooling in an ice bath, 1.56 mol/L n-hexane solution of n-butyllithium, 3.5 ml (5.5 mmol), was dropwise added. The contents were stirred at room temperature in a nitrogen atmosphere for 1 day. With the flask cooled in a dry ice/methanol bath, a solution of 6,6-bis(4-tert-butylphenyl)fulvene 1.78 9 (5.20 mmol) in 20 ml of tetrahydrofuran, was dropwise added to the solution by means of the dropping funnel over a period of 20 minutes. The liquid temperature was then slowly raised to room temperature, and the solution was stirred in a nitrogen atmosphere at the temperature for 3 days. Then, a saturated aqueous solution of ammonium chloride 100 ml and diethyl ether 100 ml were gradually added to the solution in this order. The resulting two-phase solution was poured into a 300 ml separation funnel, and the funnel was shaken several timessothatthewaterphasewasremoved. Theobtainedorganic phase was washed three times with water 100 ml and once with a saturated salt solution 100 ml, and dried over anhydrous magnesium sulfate. The solution was filtered to remove solids, and the solvent of the filtrate was distilled away. The residual solid was washed with n-hexane to give 2.664 g of bis(4-tert-butylphenyl)cyclopentadienyl(octamethyloctahydrodibenzofluorenyl)methane as a white solid (3.65 mmol, 70.1% yield). Identification of the bis(4-tert-butylphenyl)cyclopentadienyl(octamethyloctahydrodibenzofluorenyl)methane was made by 1H NMR and the FD-mass spectrometric analysis, the results being given below:
