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Methaneseleninic acid : ウィキペディア英語版
Methaneseleninic acid

Methaneseleninic acid (methylseleninic acid or MSA) is a seleninic acid with the chemical formula CH3SeO2H).
==Preparation==
Methaneseleninic acid is conveniently synthesized through oxidation (3% hydrogen peroxide) of commercially available dimethyl diselenide.〔Ip, C.; Thompson, H.J.; Zhu, Z.; Ganther, H.E. "In vitro and in vivo studies of methylseleninic acid: evidence that a monomethylated selenium metabolite is critical for cancer chemoprevention". ''Cancer Res.'' 2000, 60, 2882–2886.〕
:MeSeSeMe + H2O2 → 2 MeSeO2H
Seleninic acids can be prepared by oxidation of selenoesters with one equivalent of dimethyldioxirane (DMDO). Use of excess DMDO affords little studied selenonic acids (RSeO3H).〔Abdo, M.; Knapp, S. "Biomimetic seleninates and selenonates." ''J. Am. Chem. Soc.'' 2008, 130, 9234–9235. 〕
:RSeC(O)R' + DMDO → RSeO2H
:RSeC(O)R' + excess DMDO → RSeO3H
Selenenic acids, formed during the ''syn''-elimination of selenoxides, undergo spontaneous disproportionation into the corresponding seleninic acids and diselenides:
:2 RSeOH → RSeO2H + 1/2 RSeSeR

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