100 responded to the intenaity of this multiplet. Also the lower intensit> of the methyl and niethjlene doublets for compound VI1 corresponded to the low intensity of the multiplet at 8 = 4.98 p.p.m. for CH,==C. There ~ ; ialso i obtained IO g. 01' r-butbl chloride. b.p. 50-54", from experiment 9 in which 235 g. of crude, high-boiling product was obtained. The phosphorus trichloride-rinI.lc)clohexene experiment was run i n the batch process apparatus described above. A charge of 51.5 g. of vinylcyclohexene, freshly washed with ferrous sulfate solution and disti!led o\er sodium and 385 g. of redistilled phosphorus trichloride, was flushed K i t h nitrogen and then irradiated
I'm 16 hr. a t 55'. Unreacted reagents were removed by dirrillation at atmospheric pressure. Vacuum distillation yielded 20 g. of 1 :1 product, b.p. l0C!2OC (4mm.), H ~ 1.5475. ~ D Aizal. Calcd. for CsH:?Cl3P: CI. 43.4; P. 12.6. F o ~ i i d : CI. 42.5: 1'. 12.7. The higher boiling product Iefi as a residue amounted to 4 g. Phosphorus trichloride reactions with the olefins listed in Table 11 2nd with those reported above to yield little or no product were r u n in the batch apparatus in a maimer similar to the experiments with isobutylene and vinylcyclohexene above except that product residues after removal oi'unreacted reagents were not distilled. An attempt to distill a portion of the phosphorus trichloride- vinyl acetate product under vacuum resulted in decomposition.
Amination of Alkylbenzenes with Trichloramine-Aluminum Chloride. Synthetic Utility and Theoretical Aspects132 Peter Kovacic, Joseph A. Levisky, and Christian T. Goralski3
Contribution from the Department of Chemistry, Case Institute of Technology, Cleveland, Ohio 44106. Received August 17, 1965 Abstract: Direct amination of monoalkylbenzenes with trichloramine in the presence of aluminum chloride provided in-alkylanilines as the predominant basic product. Yields varied from
