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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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  <dc:creator>Taylor, Wesley G.</dc:creator>
  <dc:creator>Schreck, Carl E.</dc:creator>
  <dc:date>1985-05-01</dc:date>
  <dc:description>Fourteen stereoisomeric mixtures of six oxazolidine heterocycles and one amino alcohol were obtained from commercial samples of (+)−, (−)−, or (±)-citronellol (2) and evaluated in a cloth test system as mosquito repellents. A technical sample of 3-acetyl-2-(2′, 6′-dimethyl-5′-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 (+)−2, was considerably more effective than standard insect repellents in bioassays with three mosquito species.</dc:description>
  <dc:identifier>https://zenodo.org/record/1229253</dc:identifier>
  <dc:identifier>10.1002/jps.2600740508</dc:identifier>
  <dc:identifier>oai:zenodo.org:1229253</dc:identifier>
  <dc:rights>info:eu-repo/semantics/openAccess</dc:rights>
  <dc:rights>https://creativecommons.org/publicdomain/zero/1.0/legalcode</dc:rights>
  <dc:title>Chiral-Phase Capillary Gas Chromatography and Mosquito Repellent Activity of Some Oxazolidine Derivatives of (+)- and (−)-Citronello1</dc:title>
  <dc:type>info:eu-repo/semantics/article</dc:type>
  <dc:type>publication-article</dc:type>
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