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]
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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)
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| 1304471 | |
| ChEBI | |
| ChemSpider | |
| 239545 | |
PubChem CID
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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).
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Thiirenes and derivatives
editNo 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.
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