Metabolism of 4,4’-dihalogenobiphenyls

Stephen Safe; Dan Jones; Otto Hutzinge

doi:10.1039/P19760000357

Metabolism of 4,4’-dihalogenobiphenyls

Stephen Safe, Dan Jones, Otto Hutzinge

Research output: Contribution to journal › Article › peer-review

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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 language	English (US)
Pages (from-to)	357-359
Number of pages	3
Journal	Journal of the Chemical Society, Perkin Transactions 1
Issue number	4
DOIs	https://doi.org/10.1039/P19760000357
State	Published - 1976

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General Chemistry

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title = "Metabolism of 4,4{\textquoteright}-dihalogenobiphenyls",

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.",

author = "Stephen Safe and Dan Jones and Otto Hutzinge",

year = "1976",

doi = "10.1039/P19760000357",

language = "English (US)",

pages = "357--359",

journal = "Journal of the Chemical Society, Perkin Transactions 1",

issn = "1470-4358",

publisher = "Royal Society of Chemistry",

number = "4",

}

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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DO - 10.1039/P19760000357

M3 - Article

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AN - SCOPUS:0016872299

SN - 1470-4358

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EP - 359

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 4

ER -

Metabolism of 4,4’-dihalogenobiphenyls

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