PHENYL VINYL SULFOXIDE Chemical Properties

Boiling point:

93-95 °C/0.2 mmHg (lit.)

Density 

1.139 g/mL at 25 °C (lit.)

refractive index 

n20/D 1.585(lit.)

Flash point:

>230 °F

storage temp. 

2-8°C

solubility 

sol most organic solvents

form 

liquid

color 

deeply yellow

BRN 

2039218

Safety Information

Hazard Codes 

Xi

Risk Statements 

41

Safety Statements 

24/25-39-26

WGK Germany 

3

HS Code 

2930909899

MSDS

• Language:English Provider:SigmaAldrich

PHENYL VINYL SULFOXIDE Usage And Synthesis

Uses

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.

Preparation

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

General Description

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.

Precautions

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

PHENYL VINYL SULFOXIDE(20451-53-0)Related Product Information

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