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Reaction of Isolated Double Bonds with Selenium Dioxide/Hydrogen Peroxide: Formation of Novel Selenite Esters

Gerhard Knothe, Richard S. Glass, Thomas B. H. Schroeder, M. O. Bagby, David Weisleder

Abstract

All articles of this category The reaction of the SeO 2 /H 2 O 2 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 77 Se-NMR and lanthanide shift experiments showed that they are a mixture of cis/trans isomers. The SeO 2 /H 2 O 2 system thus presents a novel possibility for the synthesis of selenites. Novel intermediate selenites are isolated in SeO 2 /H 2 O based hydroxylations

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Key concepts: Chemistry, Selenium, Vicinal, Diastereomer, Hydrogen peroxide, Hydrogen bond, Sequence (biology), Proton NMR