In chemistry, a selone (also known as a selenoketone) is the structural analog of a

ketone In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

where

selenium Selenium is a chemical element; it has symbol (chemistry), symbol Se and atomic number 34. It has various physical appearances, including a brick-red powder, a vitreous black solid, and a grey metallic-looking form. It seldom occurs in this elem ...

replaces

oxygen Oxygen is a chemical element; it has chemical symbol, symbol O and atomic number 8. It is a member of the chalcogen group (periodic table), group in the periodic table, a highly reactivity (chemistry), reactive nonmetal (chemistry), non ...

. Selenium-77 is one of the

isotopes of selenium Selenium has six natural isotopes that occur in significant quantities, along with the trace isotope 79Se, which occurs in minute quantities in uranium ores. Five of these isotopes are stable: 74Se, 76Se, 77Se, 78Se, and 80Se. The last three also ...

that is stable and naturally occurring, so selenoketone-containing chemicals can be analyzed by

nuclear magnetic resonance spectroscopy Nuclear magnetic resonance spectroscopy, most commonly known as NMR spectroscopy or magnetic resonance spectroscopy (MRS), is a Spectroscopy, spectroscopic technique based on re-orientation of Atomic nucleus, atomic nuclei with non-zero nuclear sp ...

(NMR). Selones can be used as chiral derivatizing agents for ⁷⁷Se-NMR. Chiral oxazolidineselones can be used for stereoselective control of

aldol reaction The aldol reaction (aldol addition) is a Chemical reaction, reaction in organic chemistry that combines two Carbonyl group, carbonyl compounds (e.g. aldehydes or ketones) to form a new β-hydroxy carbonyl compound. Its simplest form might invol ...

s, 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. Selenobenzophenone reversibly dimerizes. It is known to undergo

cycloaddition In organic chemistry, a cycloaddition is a chemical reaction in which "two or more Unsaturated hydrocarbon, unsaturated molecules (or parts of the same molecule) combine with the formation of a cyclic adduct in which there is a net reduction of th ...

with 1,3-dienes in reactions similar to the Diels-Alder reactions.

References

{{organic-chemistry-stub Organoselenium compounds Functional groups Selenium(−II) compounds

See also

Further reading

References