Metabolism of 4,4’-dihalogenobiphenyls

Stephen Safe, Dan Jones, Otto Hutzinge

Research output: Contribution to journalArticle

39 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)357-359
Number of pages3
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number4
DOIs
StatePublished - 1976

ASJC Scopus subject areas

  • Chemistry(all)

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