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Thiirene

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Thiirene
Names
Preferred IUPAC name Thiirene
Systematic IUPAC name Thiacyclopropene
Other names Epithioethene
Ethyne sulfide
Acetylene sulfide
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 1304471
ChEBI
ChemSpider
Gmelin Reference 239545
PubChem CID
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C2H2S/c1-2-3-1/h1-2HKey: JTQAPFZZCXWQNQ-UHFFFAOYSA-N
  • InChI=1/C2H2S/c1-2-3-1/h1-2HKey: JTQAPFZZCXWQNQ-UHFFFAOYAN
SMILES
  • C1=CS1
Properties
Chemical formula C2H2S
Molar mass 58.10228
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Thiirene is an organosulfur compound with the formula C2H2S. It can be viewed as a derivative of cyclopropene, but with the methylene group replaced by sulfur. It is antiaromatic and very labile.

Thiirenes and derivatives

No thiirene has been isolated at room temperature, but they have been observed spectroscopically at low temperatures.

Thiirene-S-oxides and S-alkylthiirenium salts have been characterized by X-ray crystallography.

References

  1. Ando, Wataru; Choi, Nami; Tokitoh, Norihiro (1996). "Thiiranes and Thiirenes: Monocyclic". Comprehensive Heterocyclic Chemistry II. pp. 173–240. doi:10.1016/B978-008096518-5.00005-8. ISBN 9780080965185.
  2. Torres, M.; Clement, A.; Bertie, J. E.; Gunning, H. E.; Strausz, O. P. (1978). "Low-Temperature Matrix Isolation of Thiirenes". The Journal of Organic Chemistry. 43 (12): 2490–2493. doi:10.1021/jo00406a045.
  3. Destro, Riccardo; Lucchini, Vittorio; Modena, Giorgio; Pasquato, Lucia (2000). "X-ray Structures and Anionotropic Rearrangements of Di-tert-butyl-Substituted Thiiranium and Thiirenium Ions. A Structure−Reactivity Relationship". The Journal of Organic Chemistry. 65 (11): 3367–3370. doi:10.1021/jo991731o. PMID 10843618.
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