Selone

{{Short description|Structural analog of a ketone with selenium replacing oxygen}}

File:Selone.png

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.{{cite journal |author1=J. Peng |author2=J. D. Odom |author3=R. B. Dunlap |author4=L. A. Silks III |name-list-style=amp | title = Use of a selone chiral derivatizing agent for the absolute configurational assignment of stereogenic center | journal = Tetrahedron: Asymmetry | year=1994 | volume=5 | issue=9 | pages = 1627–1630 | doi = 10.1016/0957-4166(94)80066-9 |url=https://zenodo.org/record/1258653}} 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.{{cite journal |author1=L. Silks |author2=D. Kimball |author3=D. Hatch | title = Chiral N-Acetyl Selone-Promoted Aldol Reactions | journal = Synthetic Communications | year = 2009 | volume = 39 | issue = 4 | pages = 641–653 | doi = 10.1080/00397910802419706|s2cid=96583069 |display-authors=etal| url = https://zenodo.org/record/1234399}}

Selenobenzophenone reversibly dimerizes. It is known to undergo cycloaddition with 1,3-dienes in reactions similar to the Diels-Alder reactions.{{Cite journal| last1 = Erker | first1 = G.| last2 = Hock| last3 = Krüger| last4 = Werner| last5 = Klärner| last6 = Artschwager-Perl| title = Synthesis and Cycloadditions of Monomeric Selenobenzophenone| journal = Angewandte Chemie International Edition in English| volume = 29| issue = 9| pages = 1067| year = 1990 | doi = 10.1002/anie.199010671 | first2 = R. | first3 = C. | first4 = S. | first5 = F. G. | first6 = U.}}