Thiete

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]

Thiete
Names
Preferred IUPAC name
2H-thiete
Systematic IUPAC name
1-Thiacyclobut-2-ene
Identifiers
3D model (JSmol)
ChemSpider
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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Infobox references

Structure

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

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.

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See also
  • Dithiete - analogue with two sulfur atoms

References
  1. Leśniak, S; Lewkowski, J; Kudelska, W; Zając, A (2008). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry III. 2.07: 389–428. doi:10.1016/B978-008044992-0.00207-8.
  2. Block, E (2007). "Thietes and Derivatives". Sci. Synth. 33: 187–202.
  3. Block, E; DeWang, M (1996). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry II. 1.24: 773–802. doi:10.1016/B978-008096518-5.00024-1.
  4. Dittmer, DC; Davis, FA (1965). "Evidence for a Thiete (Thiacyclobutene)". J. Am. Chem. Soc. 87 (9): 2064–2065. doi:10.1021/ja01087a048.
  5. 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. 1B (2nd ed.). Elsevier. p. 780. ISBN 978-0-08-096518-5.
  6. Rodler, M; Bauder, A (1985). "Microwave spectrum, dipole moment and molecular structure of 1,2-dithiete". Chemical Physics Letters. 114: 575–578. doi:10.1016/0009-2614(85)85145-9.
  7. 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
  8. 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
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