Reaction of isolated double bonds with selenium dioxide/hydrogen peroxide: Formation of novel selenite esters

Gerhard Knothe, Richard S Glass, T. Benjamin Schroeder, Marvin O. Bagby, David Weisleder

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)57-60
Number of pages4
JournalSynthesis
Issue number1
Publication statusPublished - 1997

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ASJC Scopus subject areas

  • Organic Chemistry

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