フェニル ビニル スルホキシド

フェニル ビニル スルホキシド 価格

フェニル ビニル スルホキシド 化学特性,用途語,生産方法

• 外観

  無色～うすい黄色透明液体

• 使用

  Phenyl vinyl sulfoxide is used as acetylene equivalent in Diels-Alder, dipolar cycloaddition, and Michael reactions; can be deprotonated to the unsaturated α-sulfinyl carbanion; undergoes additive Pummerer reactions.

• 製造方法

  Phenyl vinyl sulfoxide can be prepared by reaction of a carbanion with chiral arylsulfinates derived from menthol or glucose, or N-sulfinyloxazolidinones of norephedrine or phenylalanine, or by sequential arylation-vinylation of sulfites derived from lactic acid or aminosulfites derived from ephedrine (99+% ee).

• Synthesis Reference(s)

  The Journal of Organic Chemistry, 61, p. 2260, 1996 DOI: 10.1021/JO960178X

• 一般的な説明

  Phenyl vinyl sulfoxide reacts with lithium enolates of ketones at -78°C in THF to yield bicyclo[n.2.0]alkan-1-ols. It also reacts with in situ generated (dialkylamino)magnesium reagent to yield symmetrical β-(dialkylamino)dithioacetals. It participates as an acetylene equivalent in Diels-Alder reactions.

• 予防処置

  As with most optically active sulfoxides, Phenyl vinyl sulfoxide racemizes in the presence of acids. Use in a fume hood.

フェニル ビニル スルホキシド 生産企業

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