Synthesis and stereochemistry of optically active selenonium imides
- 1 January 1994
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 16,p. 2257-2264
- https://doi.org/10.1039/p19940002257
Abstract
Diastereoisomeric mixtures of 4-[(–)-menthyloxycarbonyl]phenyl(methyl)selenonium-N-toluene-4′sulfonimides (dia.-1) and 4-[(–)-menthyloxycarbonyl]phenyl(2′, 4′, 6′-triisopropylphenyl)selenonium N-toluene-4″-sulfonimides (dia.-7) were synthesized. Optical resolution by the fractional recrystallization of dia.-7 from methanol gave the optically pure (–)-selenonium imide as stable crystals. The absolute configuration around the selenium atom was determined to be S based on the CD spectra. The kinetics for the epimerization by pyramidal inversion of the optically active selenonium imide were studied.Keywords
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