Peracid-mediated -oxidation and rearrangement of dimethylphosphoramides: plausible model for oxidative bioactivation of the carcinogen hexamethylphosphoramide (HMPA) |
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Authors: | Ian Holden Yoffi Segall Ella C Kimmel John E Casida |
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Institution: | Pesticide Chemistry and Toxicology Laboratory, Department of Entomological Sciences University of California, Berkeley, California 94720 U.S.A. |
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Abstract: | Dimethylphosphoramides react with -chloroperoxybenzoic acid (MCPBA) in anhydrous acetone to yield the previously unknown -dimdethylamino-oxyphosphonous derivatives -oxidation and rearrangement. Further MCPBA oxidation yields formaldehyde and nitrosomethane, isolated as its -dimer. These reactions provide a possible biomimetic model for the metabolic activation of hexamethylphosphoramide as a mutagen and carcinogen. |
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