5a -c) C6H5 ( 2 a -c ) ((1): R = R, f h j : R = R, (0: R = R A tion at the phosphorus atom, and in the case of (2c) for incorporation of the k C triple bond by thermal elimination of trimethylchloro~ilane~~]. Procedure Chlorophenyl(trimethylsily1)methane (72.4 g, 360 mmol) is converted with Mg (10.0 g, 400 mmol) in diethyl ether (200 ml) into the Grignard compound, which is then added dropwise slowly to an ice-cooled solution of PC13 (49 g, 360 mmol) in ether (150 ml). MgClz is removed by filtration and the filtrate is evaporated down under vacuum. Fractional distillation of the residue furnishes 52.7 g (55%) of (lc), b.p.A solution of (lc) (15.0 g, 57 mmol) in ether (200 ml) is treated with 25.3 g (220 mmol) of 1,4-diazabicycl0[2.2.2]0~tane and the mixture is stirred for 12 h at room temperature.The insoluble material is filtered off and washed with ether. The combined filtrates are then evaporated down under vacuum and the amine hydrochloride which precipitates is removed by filtration. After removal of solvent the residue is treated with n-pentane, filtered and the filtrate evaporated down and distilled yield 7.1 g (54%) of (2c), b.p. 51 "C/10-) torr.53"C/10-3 torr ["P('H)-NMR (C6D6): 6=189].
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