1,2-Dithietane
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| Names | |
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| Preferred IUPAC name
1,2-Dithietane | |
| Systematic IUPAC name
1,2-Dithiacyclobutane | |
| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C2H4S2 | |
| Molar mass | 92.18 g/mol |
| Related compounds | |
Related compounds
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Dithiete, Dioxetane, 1,2-Dithiadistannetane |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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1,2-Dithietane is a dithietane. It is a heterocyclic compound with a four-membered ring. Two sulfur atoms are adjacent, and the molecule is saturated. 1,2-Dithietane has not been produced as of 2000. The combination of ring strain, and lone pairs of electrons, which repel each other, on the sulfur atoms makes the sulfur-sulfur bond too weak to produce the molecule. However a few derivatives are known. 3,4-Diethyl-1,2-dithietane 1,1-dioxide has one sulfur fully oxidised. Dithiatopazine is a tricyclic compound with the -S-S- as a bridge.[1][2] 1,2-Dithietan-3-one, the ketone of 1,2-dithietane, was produced in 2008 by reacting α-dithiolactone with ethoxycarbonylformonitrile oxide.[3] 4,4-di-tert-butyl-1,2-dithietan-3-one and the spiro compound 5,5,9,9-tetramethyl-1,2-dithiaspiro[3.5]nonan-3-one have also been made.[3]
1,2-Dithietane was claimed to have been made by reacting 1,2-ethanedithiol with iodine, but the major product was an eight-membered ring.[4]
A reaction of 2,3-dimercapto-1-propanol with 3-methyllumiflavin transiently produced 3-hydroxy-1,2-dithietane. This dithietane polymerised under light, breaking and reforming the S-S bonds to form a long chain -SSCH(OH)CH2-.[5]
References
[edit]- ^ Nakayama, Juzo; Ishii, Akihiko (2000). Chemistry of dithiiranes, 1,2-dithietanes, and 1,2-dithietes. Advances in Heterocyclic Chemistry. Vol. 77. pp. 221–284. doi:10.1016/S0065-2725(00)77007-3. ISBN 9780120207770.
- ^ Nicolaou, K. C.; Hwang, C. K.; Duggan, M. E.; Carroll, P. J. (June 1987). "Dithiatopazine. The first stable 1,2-dithietane". Journal of the American Chemical Society. 109 (12): 3801–3802. doi:10.1021/ja00246a059.
- ^ a b Shigetomi, Toshiyuki; Okuma, Kentaro; Yokomori, Yoshinobu (January 2008). "First isolation of 1,2-dithietan-3-one from α-dithiolactone". Tetrahedron Letters. 49 (1): 36–38. doi:10.1016/j.tetlet.2007.11.025.
- ^ Amaratunga, Wimal; Milne, John; Santagati, Angela (1998). "Oligomerization and cyclization of 1,2-ethanedithiol (EDT), HSCH2CH2SH, by selenium dioxide and iodine". Journal of Polymer Science Part A: Polymer Chemistry. 36 (3): 379–390. doi:10.1002/(SICI)1099-0518(199802)36:3<379::AID-POLA2>3.0.CO;2-N.
- ^ Nagata, Toshiyuki; Fujimori, Ken; Oae, Shigeru (October 1992). "Proximity effect in the oxidation of dithiols with 3-methyllumiflavin". Heteroatom Chemistry. 3 (5–6): 529–534. doi:10.1002/hc.520030513.
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