Vinyl sulfone

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.^[1] Many vinyl sulfones are known.

Vinyl sulfone

Identifiers
CAS Number	77-77-0
3D model (JSmol)	Interactive image
ChEBI	CHEBI:53729
ChEMBL	ChEMBL349205
ChemSpider	6251
EC Number	201-057-6
Gmelin Reference	558721
PubChem CID	6496
UNII	5PFN71LP8M
UN number	2810 (DIVINYL SULFONE)
InChI InChI=1S/C4H6O2S/c1-3-7(5,6)4-2/h3-4H,1-2H2 Key: AFOSIXZFDONLBT-UHFFFAOYSA-N
SMILES C=CS(=O)(=O)C=C
Properties
Chemical formula	C4H6O2S
Molar mass	118.15 g·mol−1
Appearance	colorless oil
Density	1.177 g cm−3
Melting point	-26 °C
Boiling point	90–92 °C (194–198 °F; 363–365 K) 8 mmHg
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H300, H310, H314, H315, H335, H341
Precautionary statements	P203, P260, P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P319, P321, P330, P332+P317, P361+P364, P362+P364, P363, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Vinyl sulfones

Examples include phenyl vinyl sulfone,^[2] methyl vinyl sulfone,^[3] and ethyl vinyl sulfone.^[4]

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:^[5]

(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.^[6]

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.^[7]

Vinyl sulfones are Michael acceptors.^[8] Vinyl sulfones add thiols, such as cysteine residues.^[9] This same reactive nature is responsible for their major industrial use in vinyl sulfone dyes.^[10]

Phenyl vinyl sulfone has been applied to ruthenium chemistry as part of olefin metathesis reactions.^[11]

Vinyl sulfone has applications to protein purification, especially when linked with mercaptoethanol.^[12]

Commercial applications

Vinyl sulfone has uses as a molluscicide pesticide.^[13]

Safety

Like similar compounds, vinyl sulfone is a lacrymator and skin irritant. These properties are somewhat mitigated because of its low volatility.^[8]