Synthesis of 14C-Labelled and Unlabelled Coplanar Polychlorinated Biphenyls (PCBs).

1 January 1990

journal article
research article
Published by Danish Chemical Society in Acta Chemica Scandinavica

Vol. 44 (10) , 1071-1076
https://doi.org/10.3891/acta.chem.scand.44-1071

Abstract

A modified Ulman reaction is described for synthesis of the three most toxic coplanar PCBs, 3,3'',4,4''-tetrachloro[14C]biphenyl, 3,3'',4,4'',5-pentachloro[14C]biphenyl and 3,3'',4,4'',5,5''-hexachloro[14C]biphenyl. 3,3'',4,5,5''-Pentachloro[14C]biphenyl and one ortho-substituted PCB, 2,3,3''4,4''-pentachloro[14C]biphenyl, were also prepared. Methods for the preparation of unlabelled 3,3'',4,4'',5-pentachlorobiphenyl and 3,3'',4,4'',5-pentachlorobiphenyl are presented. Three isomeric tetrachloro(nitro)biphenyls were isolated and characterized as intermediates in the synthesis of 3,3'',4,4''5- and 2,3,3'',4,4''-pentachlorobiphenyl via the Ponomarenko reaction. The Cadogan diaryl coupling method was also used for synthesis of 3,3'',4,4'',5-pentachlorobiphenyl.

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