General chemical structure of a selone

In chemistry, a selone (also known as a selenoketone) is the structural analog of a ketone where selenium replaces oxygen. Selenium-77 is one of the isotopes of selenium that is stable and naturally occurring, so selenoketone-containing chemicals can be analyzed by nuclear magnetic resonance spectroscopy (NMR). Selones can be used as chiral derivatizing agents for 77Se-NMR.[1] Chiral oxazolidineselones can be used for stereoselective control of aldol reactions, analogous to the Evans aldol reaction that uses oxazolidinones, which allows 77Se-NMR to be used to determine the diastereomeric ratio of the aldol product.[2]

Selenobenzophenone reversibly dimerizes. It is known to undergo cycloaddition with 1,3-dienes in a reaction similar to the Diels-Alder reaction.[3]

References

  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). "Chiral N-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.