Thiete

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title: "Thiete" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["sulfur-heterocycles", "four-membered-rings"] topic_path: "general/sulfur-heterocycles" source: "https://en.wikipedia.org/wiki/Thiete" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 424960119 | ImageFile=Thietene.png | ImageSize=100 | PIN=2H-Thiete | OtherNames=1-Thiacyclobut-2-ene |Section1={{Chembox Identifiers | CASNo=503-31-1 | PubChem=3415867 | SMILES=C1C=CS1 | ChemSpiderID_Ref = | ChemSpiderID = 2659702 | InChI = 1/C3H4S/c1-2-4-3-1/h1-2H,3H2 | InChIKey = HPINPCFOKNNWNW-UHFFFAOYAF | StdInChI_Ref = | StdInChI = 1S/C3H4S/c1-2-4-3-1/h1-2H,3H2 | StdInChIKey_Ref = | StdInChIKey = HPINPCFOKNNWNW-UHFFFAOYSA-N |Section2={{Chembox Properties | Formula=C3H4S | MolarMass=72.12886 | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility=

Thiete is a heterocyclic compound containing an unsaturated four-membered ring with three carbon atoms and one sulfur atom. 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.

Structure

Thiete is a valence isomer of the compound thioacrolein (CH2=CHCH=S) and undergoes ring opening to it at temperatures below 400°C. Thiete has been shown to be planar, with a C-S-C angle of 76.8 degrees.

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.

Thiete 1,1-dioxides are sulfones, the parent being C3H4SO2. They are more stable than the parent thietes. Substituted thiete-1,1-dioxides can also be prepared by [2+2] cycloaddition of sulfenes and ynamines.

References

References

  1. Leśniak, S. (2008). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry III.
  2. Block, E. (2007). "Thietes and Derivatives". Sci. Synth..
  3. Block, E. (1996). "Thietanes and Thietes: Monocyclic". Comprehensive Heterocyclic Chemistry II.
  4. Dittmer, DC. (1965). "Evidence for a Thiete (Thiacyclobutene)". J. Am. Chem. Soc..
  5. (1996). "Comprehensive Heterocyclic Chemistry II". Elsevier.
  6. Rodler, M. (1985). "Microwave spectrum, dipole moment and molecular structure of 1,2-dithiete". Chemical Physics Letters.
  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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sulfur-heterocyclesfour-membered-rings