Selone information

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]

^ 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.
^ 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.
^ 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.

[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.

Selone information

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Selone

Ester

Ketone

Amine

Alkene

Benzene

Urea

Ether

Methyl group

Phenyl group

Acetal

Carboxylic acid

Chlorofluorocarbon

Ethyl group

Sulfonic acid

Iodine monobromide

Hydroxy group

Alkane

Acyl group

Ethylene

Oxime

Benzoyl group

Azo compound

Alkyl nitrite

Nitrene

Alkyl group

Carbamate

Imide

Amide