A vinyl sulfone is an organic compound with the formula O2S(CH=CH2)2. The molecule consisting of two vinyl groups bonded to a sulfone. It is the parent of several vinyl sulfones of the type O2S(CH=CH2)R. Many vinyl sulfones are known.
Vinyl sulfones Examples include phenyl vinyl sulfone, methyl vinyl sulfone, and ethyl vinyl sulfone.
Preparation Divinyl sulfone is prepared from the diacetate bis(2-hydroxyethyl)sulfide. Oxidation of this diester with hydrogen peroxide gives the sulfone. The sulfone is then pyrolyzed to induce elimination of two equivalents of acetic acid:
(AcOCH2CH2)2SO2 → (CH2=CH)2SO2 + 2 HOAc (Ac = acetyl) Other vinyl sulfones are prepared analogously to the vinyl sulfone, i.e. by H2O2-oxidation of the sulfide.
Reactions and uses Vinyl sulfones are dienophiles. Subsequent to the cycloaddition to a vinyl sulfone, the phenylsulfonyl group can be removed by reduction with zinc. Vinyl sulfones are Michael acceptors. Vinyl sulfones add thiols, such as cysteine residues. This same reactive nature is responsible for their major industrial use in vinyl sulfone dyes. Phenyl vinyl sulfone has been applied to ruthenium chemistry as part of olefin metathesis reactions. Vinyl sulfone has applications to protein purification, especially when linked with mercaptoethanol.
Commercial applications Vinyl sulfone has uses as a molluscicide pesticide.
Safety Like similar compounds, vinyl sulfone is a lacrymator and skin irritant. These properties are somewhat mitigated because of its low volatility.
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