Vinyl sulfone
A vinyl sulfone is an organic compound with the formula. The molecule consisting of two vinyl groups bonded to a sulfone. It is the parent of several vinyl sulfones of the type. 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 bissulfide. Oxidation of this diester with hydrogen peroxide gives the sulfone. The sulfone is then pyrolyzed to induce elimination of two equivalents of acetic acid: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.