| Abstract: | Several N-(2-halobenzyl)anilines and N-benzyl-2-haloanilines have been synthesized and their photochemical reactions studied. Upon irradiation, the aqueous acetonitrile solution of N-benzyl-2-chloroaniline was cyclized and reduced to give phenanthridine, 5,5′,6,6′-tetrahydro-6,6′-biphenanthridyl (THBP), N-ben-zylaniline, and bibenzyl. Similar products were produced in the photochemical reactions of other halo-genated N-benzylanilines, except iodo-substituted N-benzylanilines. No dimer (THBP) was produced from the iodo-substituted N-benzylanilines. Both singlet and triplet states are involved in the photochemical reactions of the haloarenes. |
