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Sulfolene information


Sulfolene[1]
Skeletal formula of sulfolene
Ball-and-stick model of the sulfolene molecule
Names
Preferred IUPAC name
2,5-Dihydro-1H-1λ6-thiophene-1,1-dione
Other names
2,5-Dihydrothiophene 1,1-dioxide
Butadiene sulfone
3-Sulfolene
Identifiers
CAS Number
  • 77-79-2 checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 6253
ECHA InfoCard 100.000.964 Edit this at Wikidata
PubChem CID
  • 6498
UNII
  • Z6003L44MN checkY
CompTox Dashboard (EPA)
  • DTXSID6021294 Edit this at Wikidata
SMILES
  • C1C=CCS1(=O)=O
Properties
Chemical formula
C4H6O2S
Molar mass 118.15 g·mol−1
Melting point 65 to 66 °C (149 to 151 °F; 338 to 339 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

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.[2] The compound is used as a source of butadiene.[3]

  1. ^ Sulfolene at Sigma-Aldrich
  2. ^ J. M. McIntosh (2001). "3-Sulfolene". E-EROS Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rs130. ISBN 0471936235.
  3. ^ Sample, Thomas E.; Hatch, Lewis F. (Jan 1968). "3-Sulfolene: A Butadiene Source for a Diels-Alder Synthesis". Journal of Chemical Education. 45 (1): 55. doi:10.1021/ed045p55.

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Sulfolene

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Sulfolene, or butadiene sulfone is a cyclic organic chemical with a sulfone functional group. It is a white, odorless, crystalline, indefinitely storable...

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Sulfolane

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butadiene to react with sulfur dioxide via a cheletropic reaction to give sulfolene. This was then hydrogenated using Raney nickel as a catalyst to give sulfolane...

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Sulfone

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dioxide to buta-1,3-diene followed by hydrogenation of the resulting sulfolene. Sulfones are prepared under conditions used for Friedel–Crafts reactions...

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Cheletropic reaction

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thermodynamic control (≥ -40 °C), the reaction produces the corresponding sulfolene through a cheletropic reaction. The activation enthalpy for the hetero-Diels–Alder...

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Raney nickel

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adiponitrile to hexamethylenediamine; Olefins to paraffins, for example, sulfolene to sulfolane; Acetylenes to paraffins, for example, 1,4-butynediol to...

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Pentadiene

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undergoes a variety of cycloaddition reactions. For example, it forms a sulfolene upon treatment with sulfur dioxide. Pentadienyl refers to the organic...

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Piperylene

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positional isomers of pentadiene. Piperylene is a typical diene. It forms a sulfolene upon treatment with sulfur dioxide. Piperylene is the product of the decarboxylation...

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Butadiene

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It can be produced by the retro-Diels-Alder reaction of cyclohexene. Sulfolene is a convenient solid storable source for 1,3-butadiene in the laboratory...

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