Lane and SpeierLithium in Ammonia Reduction of 1-Bromonorbornane with Inverse Addition. A solution of 134.8 mg (19.5 mmol) of lithium metal in 60 ml of twice-distilled ammonia3I was added dropwise to a rapidly stirred solution of 351.1 mg (2.00 mmol) of 1-bromonorbornane in 50 ml of doubly-distilled ammonia and 10 ml of dry diethyl ether. The characteristic blue color of lithium in ammonia was immediately discharged upon addition to the halide solution. Following the addition, excess lithium was destroyed with solid ammonium chloride as described above. GLC analysis of the ethereal residue revealed 90.6% norbornane and 9.4% 1,l'-binorbornane.Lithium in Ammonia Reduction of 1-Bromonorbornane at High Dilution. A solution of 500 mg (2.86 mmol) of 1-bromonorbornane in 50 ml of dry diethyl ether was diluted with 150 ml of twice-distilled ammonia31 and added dropwise to a rapidly stirred solution of 250 ml(35.7 mmol) of lithium in a mixture consisting of 500 ml of twice-distilled ammonia3I and 100 ml of dry diethyl ether at reflux. Following the addition, the reaction mixture was allowed to stir for 1 h a t reflux and was then quenched with solid ammonium chloride as described above. GLC analysis of the ethereal residue revealed 99.2% norbornane and 0.8% 1,l'-binorbornane.Registry No.--4, 59219-48-6; ciscyclopentane-1,3-dicarboxylic acid, 876-05-1; cis-cyclopentane-1,3-dicarboxylic acid chloride, 59219-49-7; cis-cyclopentane-l,3-bis(N,N-dimethylcarboxamide), 59219-50-0; trans-cyclopentane-l,3-bis(N,N-dimethylcarboxamide), 59219-51-1; 1,3-bis(dimethylamino)cyclopentane, 59219-52-2; Nmethyl-N-(1-norbornylmethyl)formamide, 59219-53-3; lithium, 7439-93-2; ammonia, 7664-41-7.