α-Hydroxy and α-Oxo Selenoamides: Synthesis via Nucleophilic Selenocarbamoylation of Carbonyl Compounds and
Toshiaki Murai1,2, Tomohiko Mizutani1, Masahiro Ebihara1
1†Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan.
Abstract:
Carbonyl compounds were added to selenocarbamoyllithiums to generate α-hydroxy and α-oxo selenoamides. Their conformations were determined by X-ray analyses. These compounds adopted conformations that were almost identical to those of ordinary amides. Unlike the consistency of the chemical shifts of the C═Se groups of the selenoamides in (13)C NMR spectra and the (1)J coupling constants of the C═Se groups, the substituents far from the selenium atom influenced the chemical shifts in (77)Se NMR.
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