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Synthesis 1997; 1997(1): 57-60
DOI: 10.1055/s-1997-1517
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Reaction of Isolated Double Bonds with Selenium Dioxide/Hydrogen Peroxide: Formation of Novel Selenite Esters

Gerhard Knothe1 , Richard S. Glass2 , T. Benjamin Schroeder2 , Marvin O. Bagby3 , David Weisleder3
  • 1National Center for Agricultural Utilization Research, U.S. Department of Agriculture, 1815 N. University Street, Peoria, Illinois 61604, U.S.A., Fax +1(309)6816686; E-mail: knotheg@ncaur.gov
  • 2Department of Chemistry, The University of Arizona, Tucson, Arizona 85721, U.S.A.
  • 3National Center for Agricultural Utilization Research, U.S. Department of Agriculture, 1815 N. University Street, Peoria, Illinois 61604, U.S.A.
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Publikationsdatum:
31. Dezember 2000 (online)

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The reaction of the SeO2/H2O2 system with long-chain olefinic compounds was investigated. The products sequence is epoxides → selenite esters → vicinal diols (threo diastereomers). Structure elucidation of the novel selenite esters by NMR studies including 77Se-NMR and lanthanide shift experiments showed that they are a mixture of cis/trans isomers. The SeO2/H2O2 system thus presents a novel possibility for the synthesis of selenites.

Novel intermediate selenites are isolated in SeO2/H2O based hydroxylations