THE PHOTOCHEMICAL-REACTIONS OF THE HALOGENATED N-BENZYLANILINES - MECHANISM OF THE REACTIONS

Several N-(2-halobenzyl)anilines and N-benzyl-2-haloanilines have been synthesized and their photochemical reactions studied. Upon irradiati on, 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-benzylaniline, and bibenzyl. Similar produc ts were produced in the photochemical reactions of other halogenated N -benzylanilines, except iodo-substituted N-benzylanilines. No dimer (T HBP) was produced from the iodo-substituted N-benzylanilines. Both sin glet and triplet states are involved in the photochemical reactions of the haloarenes.