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The photochemical reactions of the halogenated N ‐benzylanilines. Mechanism of the reactions
Author(s) -
Park YongTae,
Lee IckHyung,
Kim YoungHee
Publication year - 1994
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570310658
Subject(s) - chemistry , bibenzyl , photochemistry , phenanthridine , acetonitrile , dimer , singlet state , aqueous solution , medicinal chemistry , organic chemistry , excited state , physics , nuclear physics
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.