Thiete
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| Preferred IUPAC name
2H-Thiete | |
| Other names
1-Thiacyclobut-2-ene
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3D model (JSmol)
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PubChem CID
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| Properties | |
| C3H4S | |
| Molar mass | 72.12886 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Thiete is a heterocyclic compound containing an unsaturated four-membered ring with three carbon atoms and one sulfur atom.[1][2][3] It is more commonly encountered not on its own, but in anellated derivatives, several of which have been synthesized. Thietes are generally not very stable.[4]
Structure
[edit | edit source]Thiete is a valence isomer of the compound thioacrolein (CH2=CHCH=S) and undergoes ring opening to it at temperatures below 400 °C.[5] Thiete has been shown to be planar, with a C-S-C angle of 76.8 degrees.[6]
Derivatives
[edit | edit source]Benzothietes are thietes annulated to benzo group. Such species are prepared by flash vacuum pyrolysis of 2-mercaptobenzyl alcohols. They are precursors to other S-heterocycles.[7]
Thiete 1,1-dioxides are sulfones, the parent being C3H4SO2. They are more stable than the parent thietes.[8] Substituted thiete-1,1-dioxides can also be prepared by [2+2] cycloaddition of sulfenes and ynamines.
See also
[edit | edit source]- Dithiete - analogue with two sulfur atoms
References
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- ^ Herbert Meier, Axel Mayer, Dieter Gröschl "Benzothietes—versatile Synthons For The Preparation Of Heterocycles" Sulfur Reports, 1994, volume 16, 23-56, Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
- ^ Thomas C. Sedergran and Donald C. Dittmer "Thiete 1,1-dioxide and Chlorothiete 1,1-dioxide" Org. Synth. 1984, vol. 62, 210.Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).