Synthesis, absolute configuration, and analysis of malathion, malaoxon, and isomalathion enantiomers
| Autor: | Clifford E. Berkman, Scott R. Perrin, Charles M. Thompson |
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| Rok vydání: | 1993 |
| Předmět: |
Insecticides
Magnetic Resonance Spectroscopy Chromatography Stereochemistry Molecular Conformation Absolute configuration Strychnine General Medicine Isomalathion Crystallography X-Ray Toxicology Chemical synthesis chemistry.chemical_compound Isomerism Malaoxon chemistry Yield (chemistry) Malathion Moiety Enantiomer Chromatography High Pressure Liquid |
| Zdroj: | Chemical Research in Toxicology. 6:718-723 |
| ISSN: | 1520-5010 0893-228X |
| DOI: | 10.1021/tx00035a018 |
| Popis: | Syntheses of the enantiomers of malathion, malaoxon, and isomalathion are reported herein. Malathion enantiomers were prepared from (R)- or (S)-malic acid in three steps. Enantiomers of malathion were converted to the corresponding enantiomers of malaoxon in 52% yield by oxidation with monoperoxyphthalic acid, magnesium salt. The four isomalathion stereoisomers were prepared via two independent pathways using strychnine to resolve the asymmetric phosphorus moiety. The absolute configurations of the four stereoisomers of isomalathion were determined by X-ray crystallographic analysis of an alkaloid salt precursor. A high-performance liquid chromatography technique was developed to resolve the four stereoisomers of isomalathion, and to determine their stereoisomeric ratios. |
| Databáze: | OpenAIRE |
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