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

doi:10.1055/s-1997-1517

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

Chemistry and Biochemistry

Research output: Contribution to journal › Article › peer-review

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 language	English (US)
Pages (from-to)	57-60
Number of pages	4
Journal	Synthesis
Issue number	1
DOIs	https://doi.org/10.1055/s-1997-1517
State	Published - 1997

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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

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.",

author = "Gerhard Knothe and Glass, {Richard S.} and Schroeder, {T. Benjamin} and Bagby, {Marvin O.} and David Weisleder",

year = "1997",

doi = "10.1055/s-1997-1517",

language = "English (US)",

pages = "57--60",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme Verlag",

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T1 - Reaction of isolated double bonds with selenium dioxide/hydrogen peroxide

T2 - Formation of novel selenite esters

AU - Knothe, Gerhard

AU - Glass, Richard S.

AU - Schroeder, T. Benjamin

AU - Bagby, Marvin O.

AU - Weisleder, David

PY - 1997

Y1 - 1997

N2 - 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.

AB - 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.

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UR - http://www.scopus.com/inward/citedby.url?scp=0031038996&partnerID=8YFLogxK

U2 - 10.1055/s-1997-1517

DO - 10.1055/s-1997-1517

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SP - 57

EP - 60

JO - Synthesis

JF - Synthesis

IS - 1

ER -

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

Abstract

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