Photodechlorination of methoxychlor induced by hydroquinone: Rearrangement and conjugate formation |
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Authors: | Sunil K Chaudhary Reginald H Mitchell Paul R West Michael J Ashwood-Smith |
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Institution: | Department of Chemistry, Environmental Toxicology Group, University of Victoria, P.O. Box 1700 Victoria, B.C., Canada, V8W 2Y2;Department of Biology, Environmental Toxicology Group, University of Victoria, P.O. Box 1700 Victoria, B.C., Canada, V8W 2Y2 |
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Abstract: | Reductive degradation of the pesticide methoxychlor by photolysis in the presence of hydroquinone in dilute solutions of acetonitrile or 1:1 aqueous t-butanol leads to processes other than simple dechlorination. Direct radical coupling with hydroquinone forms a markedly estrogenic conjugate. A pH dependant molecular rearrangement gives pro-estrogenic 4,4′-dimethoxy-α,α′-dichlorostilbenes, and condensation with hydroquinone yields the chlorine free polycyclic aromatic, 12-hydroxy-3,6-dimethoxybenzob]phenanthro9,10-d]furan. |
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