T. Nishiwaki, M. Usui, Kinji Anda
Mar 1, 1979
Citations
0
Influential Citations
26
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
2,4,6-Trichlorobiphenyl and seven other chlorobiphenyls have been photolyzed in both alkaline and neutral 2-propanol in order to investigate the reactivity and selectivity towards dechlorination. Predominant dechlorination at the 2-position has been confirmed for all PCBs in neutral solution and interpreted in terms of the steric and electronic effects of the phenyl group. In the presence of alkali, however, competitive elimination between the ortho and para chlorine atoms of 2,4-dichlorobiphenyl and 2,4,6-trichlorobiphenyl occurred. The photo-dechlorination of 2,3- and 2,5-dichlorobiphenyls took place however only at the ortho position. The dechlorination ratios (ortho/para) were 7.5 and 0.8 for 2,4-dichlorobiphenyl and 2,4,6-trichlorobiphenyl, respectively. This characteristic of the ortho chlorine atom has been elucidated assuming the steric and electronic effects of the phenyl group in the radical anion. A correlation has been found between the reduction potential and the reactivity of PCB in alkaline...