# Selone

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{{Short description|Structural analog of a ketone with selenium replacing oxygen}}
thumb|100px|right|General chemical structure of a selone
In chemistry, a '''selone''' (also known as a '''selenoketone''') is the structural analog of a [ketone](/source/ketone) where [selenium](/source/selenium) replaces [oxygen](/source/oxygen). Their primary application is for [chemical analysis](/source/chemical_analysis).  

Selenium-77 is one of the [isotopes of selenium](/source/isotopes_of_selenium) that is [stable and naturally occurring](/source/Natural_isotopes), so selenoketone-containing chemicals can be analyzed by [nuclear magnetic resonance spectroscopy](/source/nuclear_magnetic_resonance_spectroscopy) (NMR). Selones can be used as [chiral derivatizing agent](/source/chiral_derivatizing_agent)s for <sup>77</sup>Se-NMR.<ref>{{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}}</ref> Chiral oxazolidineselones can be used for [stereoselective](/source/stereoselective) control of [aldol reaction](/source/aldol_reaction)s, analogous to the [Evans aldol](/source/Evans_aldol) reaction that uses [oxazolidinone](/source/oxazolidinone)s, which allows <sup>77</sup>Se-NMR to be used to determine the [diastereomeric ratio](/source/diastereomeric_ratio) of the aldol product.<ref>{{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}}</ref>

Selenobenzophenone reversibly dimerizes. It is known to undergo [cycloaddition](/source/cycloaddition) with 1,3-dienes in reactions similar to the [Diels-Alder reaction](/source/Diels-Alder_reaction)s.<ref>{{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.}}</ref>

==See also==
* [Thioketone](/source/Thioketone)
* [Telluroketone](/source/Telluroketone)

==Further reading==
* [http://goldbook.iupac.org/S05588.html Definition of Selones in the IUPAC Gold Book]

==References==
{{reflist}}

{{Functional group}}
{{organic-chemistry-stub}}

Category:Organoselenium compounds
Category:Functional groups
Category:Selenium(−II) compounds

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Adapted from the Wikipedia article [Selone](https://en.wikipedia.org/wiki/Selone) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Selone?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.