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 上流と下流の製品情報
原材料
準備製品