Gamma-Radiolysis of Tertiary Aromatic Amines.
Final technical rept. 1 Oct 71-30 Sep 72,
NEWCASTLE-UPON-TYNE UNIV (ENGLAND) DEPT OF ORGANIC CHEMISTRY
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Earlier research on the gamma-radiolysis of 1-phenylpiperidine has been extended to give evidence of the formation of the enamine 1-phenyl-2-piperideine as an intermediate. Thus, irradiation of the amine in the presence of N-phenylmaleimide yields 1,2,3,4,5,6-hexahydro-4aH-benzo cquinolizine-5-6-N-phenyldicarboximide but if the amine is first irradiated in the pure state, and subsequently treated with N-phenylmaleimide, an isomeric product is obtained. Gamma-radiolysis of, or reaction of t-butoxy radicals with 1-phenylhexahydroazepine yields the radical coupling dimer 1,1diphenyldodecahydro-2,2-biazepine. A number of 2-arylhexahydroisoindolines and 2-p-tolyloctahydrocyclopenta cpyrrole were also prepared. Reaction of compounds with t-butoxy radicals afforded dimeric products analogous to one obtained from 1-phenylpyrrolidine.
- Radiation and Nuclear Chemistry