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benzeneselenol : ウィキペディア英語版
benzeneselenol

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Benzeneselenol is the organoselenium compound with the formula C6H5SeH, often abbreviated PhSeH. It is the selenium analog of the simple aromatic alcohol phenol, and the related thiol thiophenol. This colourless, intensely malodorous compound is a useful reagent in organic synthesis.〔
==Synthesis and basic properties==
Benzeneselenol is prepared via the reaction of phenylmagnesium bromide and selenium:
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More so than thiophenol, benzeneselenol is easily oxidized by air. The product is diphenyl diselenide as shown in this idealized equation:
: 4 PhSeH + O2 → 2 PhSeSePh + 2 H2O
The presence of the diselenide is indicated by a yellow coloration in most samples of PhSeH. The diselenide can be converted back to the selenol by reduction followed by acidification of the resulting PhSe.
PhSeH is approximately seven times more acidic than the related thiophenol. Both compounds dissolve in water upon the addition of base.
In organic synthesis benzeneselenol is converted to its conjugate base PhSe, a potent nucleophile.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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