Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Synthesis and Stereochemistry of Optically Active Selenoxides
Nobumasa KAMIGATAToshio SHIMIZU
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1990 Volume 48 Issue 3 Pages 229-239

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Abstract
Some optically active diaryl selenoxides stabilized by bulky oitho substituents such as isopropyl or t-butyl group were obtained by fractionary recrystallization or by chromatographic resolutions. Optically active alkyl aryl selenoxides were synthesized by asymmetric oxidation of corresponding selenides under Sharpless oxidation conditions The absolute configurations of these optically active selenoxides were determined by X-ray diffraction and circular dichroism spectra. The rate of racemization of the optically active selenoxide under several conditions were investigated, and the mechanism involving achiral hydrate was clarified by H218O studies.
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© The Society of Syhthetic Organic Chemistry, Japan
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