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Chiral-Phase Capillary Gas Chromatography and Mosquito Repellent Activity of Some Oxazolidine Derivatives of (+)- and (−)-Citronello1

Taylor, Wesley G.; Schreck, Carl E.


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{
  "DOI": "10.1002/jps.2600740508", 
  "author": [
    {
      "family": "Taylor, Wesley G."
    }, 
    {
      "family": "Schreck, Carl E."
    }
  ], 
  "issued": {
    "date-parts": [
      [
        1985, 
        5, 
        1
      ]
    ]
  }, 
  "abstract": "Fourteen stereoisomeric mixtures of six oxazolidine heterocycles and one amino alcohol were obtained from commercial samples of (+)\u2212, (\u2212)\u2212, or (\u00b1)-citronellol (2) and evaluated in a cloth test system as mosquito repellents. A technical sample of 3-acetyl-2-(2\u2032, 6\u2032-dimethyl-5\u2032-heptenyl)oxazolidine (1), evaluated initially as a mixture of two pairs of enantiomers, was an effective repellent against two of the three species of mosquitoes. To study repellency-stereochemistry relationships, 1 was isolated as fractions G-1, G-2, I-1, and I-2, corresponding to representative samples of the four possible stereoisomers. The enantiomeric composition of 1, but not of the other derivatives, could be determined by chiral-phase capillary gas chromatography with Chirasil-Val. Two chiral phases showed that experimental samples of 1, and hence the commercial samples of 2, were composed of not more than 90% of one enantiomer. Differences in repellency of isomerically enriched samples were generally small. Fraction G, a mixture of diastereoisomers readily prepared from (+)\u22122, was considerably more effective than standard insect repellents in bioassays with three mosquito species.", 
  "title": "Chiral-Phase Capillary Gas Chromatography and Mosquito Repellent Activity of Some Oxazolidine Derivatives of (+)- and (\u2212)-Citronello1", 
  "type": "article-journal", 
  "id": "1229253"
}
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