3-sulfolene

Also known as 2,5-dihydrothiophene-1,1-dioxide

Sulfolene, or butadiene sulfone is a cyclic organic chemical with a sulfone functional group. It is a white, odorless, crystalline, indefinitely storable solid, which dissolves in water and many organic solvents. The compound is used as a source of butadiene.

Wikidata facts

Mass: 118.009

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melting point: 65.0
canonical SMILES: C1C=CCS1(=O)=O
chemical formula: C₄H₆O₂S
Commons category: 3-Sulfolene

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Article

13 sections

Contents

Production
Reactions
Acid-base reactivity
Isomerization to 2-sulfolene
Hydrogenation
Halogenation
Diels-Alder reactions
2- and 3-Sulfolenes as a dienophile
Other cycloadditions
Polymerization
3-Sulfolene as a recyclable solvent
Uses
References

== Production == 350px|center|Synthesis of sulfolene Sulfolene is formed by the cheletropic reaction between butadiene and sulfur dioxide. The reaction is typically conducted in an autoclave. Small amounts of hydroquinone or pyrogallol are added to inhibit polymerization of the diene. The reaction proceeds at room temperature over the course of days. At 130 °C, only 30 minutes are required. An analogous procedure gives the isoprene-derived sulfone.