화학공학소재연구정보센터
Journal of Applied Electrochemistry, Vol.27, No.12, 1390-1393, 1997
Electroreductive Aromatization of Imines and Diimines
4-Methyl-4-trichloromethyl-p-quinone-(1)-arylimines (1a-1d) undergo the cathodic elimination of a trichloromethyl group to give the corresponding N-tolylarylamines (2a-2d), whose yields were strongly dependent on the kind of electrode materials. The yield of 2a increased in the sequence : Hg < Pt < glassy carbon < graphite felt of Toyoubo Corp (GF-T) < graphite felt of National Electric Carbon Corp (GF-N). Modification of GF-T with zinc or bismuth was effective in giving 2a in a higher yield. Similarly, electroreduction of 1,1-bis [p-(4-methyl-4-trichloromethyl-2,5-cyclohexadienone-(1)-iminyl) phenyl]cyclohexane (3a) and -4-methylcyclohexane (3b) gave 1,1-bis[4-N-p-tolylaminophenyl]-cyclohexane (4a) and -4-methylcyclohexane (4b) by the elimination of two trichloromethyl groups together with 1-[4-N-p-tolylamino-phenyl]-1-[p-(4-methyl-4-trichloromethyl-2,5-cyclohexadienone-(1)-iminyl)phenyl]cyclohexane (5a) and -4-methylcyclohexane (5b) as by-products.