Thiirene

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 ;
ChemSpider	4574411 ;
Gmelin Reference	239545
PubChem CID	5461041;
CompTox Dashboard (EPA)	DTXSID00420123 ;
	InChI InChI=1S/C2H2S/c1-2-3-1/h1-2H Key: JTQAPFZZCXWQNQ-UHFFFAOYSA-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). verify (what is ?) Infobox references

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

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

Thiirene-S-oxides and S-alkylthiirinium 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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[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.