Thiirene

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.^[1]

Thiirene
Names

Preferred IUPAC name Thiirene
Systematic IUPAC name Thiacyclopropene
Other names Epithioethene Ethyne sulfide Acetylene sulfide
Identifiers
CAS Number	157-20-0
3D model (JSmol)	Interactive image
Beilstein Reference	1304471
ChEBI	CHEBI:30976^Y
ChemSpider	4574411^Y
Gmelin Reference	239545
PubChem CID	5461041
CompTox Dashboard (EPA)	DTXSID00420123
InChI InChI=1S/C2H2S/c1-2-3-1/h1-2H^N Key: JTQAPFZZCXWQNQ-UHFFFAOYSA-N^N InChI=1/C2H2S/c1-2-3-1/h1-2H Key: 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 [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Thiirenes and derivatives

No thiirene has been isolated at room temperature, but they have been observed spectroscopically at low temperatures.^[2]

Thiirene-S-oxides and S-alkylthiirenium salts have been characterized by X-ray crystallography.^[3]

References

^ 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.

^ 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.

^ 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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