4138FINNEGAN AND KUTTA VOL,. The V.P.C. (silicone gum rubber at 100') of both the crude and the distilled product showed one peak whose retention time was identical with that of an authentic sample. In a blank experiment, a solution of 0.05 mole of nitrile I11 ( R = n-C4Hg) and 0.1 mole of n-butyl bromide in 25 ml. of ether was added to 0.1 mole of sodamidell in 150 ml. of liquid ammonia. After 3 hr., excess ammonium chloride was added, and the reaction mixture was worked up as described above. Distillation of the crude product afforded 9.99 g. (87%) of recovered starting nitrile, b.p. 135-136" (3.8 mm.),15 which was indicated to be pure by V.P.C.The blank experiment was repeated omitting the n-butyl bromide. After the ammonia was evaporated, water and ether were added. The solid was collected, dried, and recrystallized successively from 957, ethanol, methanol, and water to afford 5.21 g. of product, m.p. 226-230", which appeared t o be a mixture of a,a-di-n-butylphenylacetamidine and a,a-di-n-butylphenylacetamide. None of the original nitrile I11 was recovered. The infrared spectrum of the solid showed, besides aromatic and aliphatic absorptions, bands a t 3500-3000 (NH) and 1725-1550 cm.-l (C=N and C 4 ) ; nitrile absorption was absent. An analysis of the solid for nitrogen (9.23%) suggested a mixture of 56% amidine and 44Y0 amide; however, neither compound was isolated.B. By Sodium Hydride.-To a stirred slurry of 17.48 g. (0.4 mole) of sodium hydride reagent13 in 200 ml. of refluxing monoglyme, under dry nitrogen, was added a solution of 11.7 g. (0.1 mole) of phenylacetonitrile and 54.8 g. (0.4 mole) of n-butyl bromide in 100 ml. of monoglyme over a period of 30 min. Refluxing was continued for 3 hr., and the reaction mixture was then worked up as described above for monoalkylations of phenylacetonitrile by means of sodium hydride. Distillation of the crude product yielded 21.8 g. (95%) of a,a-di-n-butylphenylacetonitrile (111, R = n-C4Hg), b.p. 134-136' (3.5 mm.).16 Both the crude and the distilled product were indicated to be pure by V.P.C. as in the corresponding experiment with sodamide.The corresponding reaction with benzyl chloride was effected similarly. Fractionation of the resulting crude product afforded (15) N. Sperber, D. Papa, and E. Schwenk, J . Am. Chem. Soc., 70, 3091 (1948).8.48 g. (417,) of 2,3-diphenylpropionitrile, b.p. 160-163' (3.5 mm.),3 and 17.22 g. (58%) of 1,2,3-triphenyl-2-cyanopropane, b.p. 215-218' (3.5 mm.), lita3 b.p. 185186' (0.6 mm.). Each product exhibited one V.P.C. peak whose retention time was identical with that of an authentic sample.Alkylation of 2-Phenylhexanenitrile with Benzyl Chloride .-To a stirred suspension of 0.05 mole of sodamidell in 250 ml. of anhydrous liquid ammonia was added a solution of 9.68 g. (0.05 mole) of 2-phenylhexanenitrile (11, R = n-C4Hg)'6 in 15 ml. of anhydrous ether. After the reaction mixture had been stirred for 2 hr., it was worked up essentially as described above for monoalkylations of phenylacetonitrile by means of sodamide. The resulti...