Download PDF
Synthesis 1997; 1997(1): 57-60
DOI: 10.1055/s-1997-1517
paper
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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.
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

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