TY - JOUR
T1 - Metabolism of 4,4’-dihalogenobiphenyls
AU - Safe, Stephen
AU - Jones, Dan
AU - Hutzinge, Otto
PY - 1976
Y1 - 1976
N2 - 4,4'-Dichlorobiphenyl in rabbits gave three major urinary metabolites: 4,4'-dichlorobiphenyl-3-ol, 3,4'-dichlorobiphenyl-4-ol, and 4'-chlorobiphenyl-4-ol. 4,4'-Dibromobiphenyl gave the bromo analogues of the three 4,4'-dichlorobiphenyl metabolites. These results are consistent with 3,4-epoxidation of the biphenyl nucleus followed by epoxide ring opening accompanied by a 1,2-halogen shift (NIH shift). 4,4'-Di-iodobiphenyl gave only a single metabolite, 4,4'-di-iodobiphenyl-3-ol, and rearrangement products were not observed.
AB - 4,4'-Dichlorobiphenyl in rabbits gave three major urinary metabolites: 4,4'-dichlorobiphenyl-3-ol, 3,4'-dichlorobiphenyl-4-ol, and 4'-chlorobiphenyl-4-ol. 4,4'-Dibromobiphenyl gave the bromo analogues of the three 4,4'-dichlorobiphenyl metabolites. These results are consistent with 3,4-epoxidation of the biphenyl nucleus followed by epoxide ring opening accompanied by a 1,2-halogen shift (NIH shift). 4,4'-Di-iodobiphenyl gave only a single metabolite, 4,4'-di-iodobiphenyl-3-ol, and rearrangement products were not observed.
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U2 - 10.1039/P19760000357
DO - 10.1039/P19760000357
M3 - Article
C2 - 814131
AN - SCOPUS:0016872299
SP - 357
EP - 359
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 1470-4358
IS - 4
ER -