Iron and copper salts catalyzed the reaction of benzylamine with CCl4 to give a mixture of 2,4,5-triphenylimidazole (1), 1-benzyl-2,4,5-triphenylimidazole (2), 2,4,5-triphenylimidazoline (3), and 1-benzyl-2,4,5-triphenylimidazoline (4) in high yields. The imidazoline 4 was obtained as the main product. The imidazole and imidazoline derivatives were also formed by the iron-catalyzed reaction of benzylidenebenzylamine (8) or dibenzylamine (5) with CCl4. The imidazoline 4 slowly underwent debenzylation and dehydrogenation with the aid of CCl4 and iron catalyst to give 1 and 2. From these results, a mechanism involving formation of 5 and 8, subsequent oxidative dimerization of 5 and 8 to form 4, and further conversion of 4 to 1, 2, and 3 is proposed.
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