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・ Selenicereus hamatus
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Seleninic acid
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Seleninic acid : ウィキペディア英語版
Seleninic acid

A seleninic acid is an organoselenium compound and an oxoacid with the general formula RSeO2H, where R ≠ H. It is a member of the family of organoselenium oxoacids, which also includes selenenic acids and selenonic acids, which are RSeOH and RSeO3H, respectively. The parent member of this family of compounds is methaneseleninic acid (CH3SeO2H), also known as methylseleninic acid or "MSA".
==Reactions and applications in synthesis==
Seleninic acids (particularly areneseleninic acids) are useful catalysts for hydrogen peroxide epoxidations, Baeyer–Villiger oxidations, oxidations of thioethers, etc.; peroxyseleninic acids (RSe(O)OOH) are thought to be the active oxidants.〔ten Brink, G.-J.; Fernandes, B. C. M.; van Vliet, M. C. A.; Arends, I. W. C. E.; Sheldon, R. A. "Selenium catalyzed oxidations with aqueous hydrogen peroxide. Part I. Epoxidation reactions in homogeneous solution." ''J. Chem. Soc., Perkin Trans.'', 1 2001, 224–228. 〕〔ten Brink, G.-J.; Vis, J.-M.; Arends, I. W. C. E.; Sheldon, R. A. "Selenium-Catalyzed Oxidations with Aqueous Hydrogen Peroxide. 2. Baeyer-Villiger Reactions in Homogeneous Solution." ''J. Org. Chem.'' 2001, 66, 2429–2433. 〕〔 Mercier, E. A.; Smith, C. D.; Parvez, M.; Back, T. G. "Cyclic Seleninate Esters as Catalysts for the Oxidation of Sulfides to Sulfoxides, Epoxidation of Alkenes, and Conversion of Enamines to α-Hydroxyketones." ''J. Org. Chem'' 2012, 77, 3508–3517. 〕

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