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United States Department of Agriculture

Agricultural Research Service

Title: Reaction of Isolated Double Bonds with Selenium Dioxide/hydrogen Peroxide. Formation and Characterization of Novel Selenite Esters

item Knothe, Gerhard
item Glass, Richard - DEPT OF CHEM., U OF ARIZ
item Schroeder, T - DEPT OF CHEM., U OF ARIZ
item Bagby, Marvin
item Weisleder, David

Submitted to: Synthesis
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: June 29, 1996
Publication Date: N/A

Interpretive Summary: In the interest of making compounds suitable as additives in commercial products such as lubricants, greases and biodiesel, several fatty compounds (materials derived from vegetable oils) were reacted with selenium dioxide and hydrogen peroxide. Accidentally, a new kind of compound was discovered in the course of this reaction which incorporates selenium. The isolation and characterization of the new compounds is described in this work. Such compounds may have different applications than expected, which the authors will attempt to define in cooperation with other researchers.

Technical Abstract: The reaction of the SeO2/H2O2 system with olefinic long-chain 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.

Last Modified: 3/29/2015
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