// Workers AI · dad joke modeWhat did Thiete say to his date? Tie-ted up.
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| Names | |
|---|---|
| Preferred IUPAC name
2H-Thiete | |
| Other names
1-Thiacyclobut-2-ene | |
| Identifiers | |
3D model (JSmol) |
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| ChemSpider | |
PubChem CID |
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CompTox Dashboard (EPA) |
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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]Thiete is a valence isomer of the compound thioacrolein (CH2=CHCH=S) and undergoes ring opening to it when heated at temperatures below 400 °C.[3]: 780 Thiete has been shown to be planar, with a C-S-C angle of 76.8 degrees.[5]
In principle, deprotonation should give a cyclic, planar anion with 6 π electrons, satisfying the Hückel criteria for aromaticity. Computer simulations in 1965 suggested that any aromatic stabilization was small, and other known approximation errors likely increased the instability. Certainly, attempts at deprotonation give only an uncharacterized mixture of decomposition products or nucleophilic substitution, even with relatively hindered bases.[6]
Derivatives
[edit]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 be prepared through oxidation of thietes, elimination of thietane dioxides, or [2+2] cycloaddition of sulfenes and ynamines.[6]: 531–535
See also
[edit]- Dithiete - analogue with two sulfur atoms
References
[edit]- ↑ Leśniak, S; Lewkowski, J; Kudelska, W; Zając, A (2008). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry III. 2 (7): 389–428. doi:10.1016/B978-008044992-0.00207-8.
- ↑ Block, E (2007). "Thietes and Derivatives". Sci. Synth. 33: 187–202.
- 1 2 Block, Eric; Wang, Ming De (1996). "Thietanes and Thietes: Monocyclic". In Katritzky, Alan R.; Rees, Charles W.; Scriven, Eric F. V. (eds.). Comprehensive Heterocyclic Chemistry II. Vol. 1B (2nd ed.). Elsevier. pp. 773–802. ISBN 978-0-08-096518-5.
- ↑ Dittmer, DC; Davis, FA (1965). "Evidence for a Thiete (Thiacyclobutene)". J. Am. Chem. Soc. 87 (9): 2064–2065. Bibcode:1965JAChS..87.2064D. doi:10.1021/ja01087a048.
- ↑ Rodler, M; Bauder, A (1985). "Microwave spectrum, dipole moment and molecular structure of 1,2-dithiete". Chemical Physics Letters. 114 (5–6): 575–578. Bibcode:1985CPL...114..575R. doi:10.1016/0009-2614(85)85145-9.
- 1 2 Dittmer, D. C.; Sedergran, T. C. (1985). "Four-membered sulfur heterocycles". Small Ring Heterocycles. Chemistry of Heterocyclic Compounds. Vol. 3. Wiley. pp. 513–514, 522–523. doi:10.1002/9780470187203. ISBN 9780471056249.
- ↑ Herbert Meier, Axel Mayer, Dieter Gröschl "Benzothietes—versatile Synthons For The Preparation Of Heterocycles" Sulfur Reports, 1994, volume 16, 23-56, doi:10.1080/01961779408048965
- ↑ Thomas C. Sedergran and Donald C. Dittmer "Thiete 1,1-dioxide and Chlorothiete 1,1-dioxide" Org. Synth. 1984, vol. 62, 210.doi:10.15227/orgsyn.062.0210