20451-53-0

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.

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).

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

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.

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