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Selone

From Wikipedia, the free encyclopedia
Structural analog of a ketone with selenium replacing oxygen
General chemical structure of a selone

In chemistry, aselone (also known as aselenoketone) is the structural analog of aketone whereselenium replacesoxygen. Their primary application is forchemical analysis.

Selenium-77 is one of theisotopes of selenium that isstable and naturally occurring, so selenoketone-containing chemicals can be analyzed bynuclear magnetic resonance spectroscopy (NMR). Selones can be used aschiral derivatizing agents for77Se-NMR.[1] Chiral oxazolidineselones can be used forstereoselective control ofaldol reactions, analogous to theEvans aldol reaction that usesoxazolidinones, which allows77Se-NMR to be used to determine thediastereomeric ratio of the aldol product.[2]

Selenobenzophenone reversibly dimerizes. It is known to undergocycloaddition with 1,3-dienes in reactions similar to theDiels-Alder reactions.[3]

See also

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Further reading

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References

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  1. ^J. Peng; J. D. Odom; R. B. Dunlap & L. A. Silks III (1994)."Use of a selone chiral derivatizing agent for the absolute configurational assignment of stereogenic center".Tetrahedron: Asymmetry.5 (9):1627–1630.doi:10.1016/0957-4166(94)80066-9.
  2. ^L. Silks; D. Kimball; D. Hatch; et al. (2009)."ChiralN-Acetyl Selone-Promoted Aldol Reactions".Synthetic Communications.39 (4):641–653.doi:10.1080/00397910802419706.S2CID 96583069.
  3. ^Erker, G.; Hock, R.; Krüger, C.; Werner, S.; Klärner, F. G.; Artschwager-Perl, U. (1990). "Synthesis and Cycloadditions of Monomeric Selenobenzophenone".Angewandte Chemie International Edition in English.29 (9): 1067.doi:10.1002/anie.199010671.
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