The Photochemical Preparation of Dimethyl-N-(2-cyano-2-propyl)ketenimine from 2,2'-Azobisisobutyronitrile¹

Abstract

decreased in the order of greater substitution of the amine group--i.e., 3" < 2' < 1". These results suggest that 111 is being catalytically deconiposed to IV and hydrogen.8 Ph3SnH -Ph3SnSnPhs + HP Experimental Allylamine and 111.-To a round bottom flask equipped with a stirrer, reflux condenser, gas inlet tube, and gas exit tube leading from the top of the condenser to a trap containing 95y0 ethanol kept a t -78" were added 32.2 g. (0.092 mole) of triphenyltin hydride and 2.6 g. (0.046 mole) of allylamine. Evolution of a gas was observed on mixing. The reaction mixture was stirred under a nitrogen atmosphere til solidification was complete. The contents of the trap gave a negative test with Nessler's reagent for ammonia, no characteristic brown-red color being observed. The solid in the flask was recrystallized from benzene, m.p. 230-232'. It did not depress the melting point on admixture with an authentic sample of 117.In a second experiment, using the same procedure as described above, 20 g. (0.057 mole) of I11 and 1.62 g. (0.029 mole) of I were used. Any possible propylene being evolved was led from the top of the condenser into a trap containing I-hexene kept at -78", but no propylene was detected upon running the trap contents into a vapor phme chromatograph.Benzylamine and 111.-The procedure of Kupchik and Connolly was followed. The first few drops of distillate collected showed bands in the infrared (cm.-l) a t 3077,

N-(2-Cyanopropan-2-yl)isobutyramide

“…Since catalytic amounts of AIBN are required when chain reactions are carried out, compounds 3and 4are almost always neither detected nor isolated. However, they have been prepared by formal synthetic methods (Smith et al, 1962).…”