Thiirene
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Names | |
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Preferred IUPAC name Thiirene | |
Systematic IUPAC name Thiacyclopropene | |
Other names Epithioethene Ethyne sulfide Acetylene sulfide | |
Identifiers | |
3D model (JSmol) | |
1304471 | |
ChEBI | |
ChemSpider | |
239545 | |
PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
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). |
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]
Thiirenes and derivatives
[edit]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
[edit]- ^ 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.