Dithiete

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

| ImageFile = Dithiete.svg | ImageFile_Ref = | ImageSize = 100 | ImageName = Kekulé, skeletal formula of dithiete with all explicit hydrogens added | PIN = 1,2-Dithiete | SystematicName = 1,2-Dithiacyclobut-3-ene | OtherNames = Dithiete Dithiacyclobutene 1,2-Dithia[4]annulene |Section1={{Chembox Identifiers | CASNo = 7092-01-5 | PubChem = 138918 | ChemSpiderID = 122516 | ChemSpiderID_Ref = | SMILES = c1css1 | SMILES1 = S1SC=C1 | StdInChI = 1S/C2H2S2/c1-2-4-3-1/h1-2H | StdInChI_Ref = | StdInChIKey = CTGHONDBXRRMRC-UHFFFAOYSA-N | StdInChIKey_Ref = |Section2={{Chembox Properties | C=2 | H=2 | S=2 |Section3={{Chembox Related | OtherFunction_label = thietes | OtherFunction = Thiete | OtherCompounds =

Dithiete is an unsaturated heterocyclic compound that contains two adjacent sulfur atoms and two sp2-hybridized carbon centers. Derivatives are known collectively as dithietes or 1,2-dithietes. With 6 π electrons, 1,2-dithietes are examples of aromatic organosulfur compounds. A few 1,2-dithietes have been isolated; one (low-yielding) route is oxidation of a dithiolene complex. 3,4-Bis(trifluoromethyl)-1,2-dithiete is a particularly stable example.

Unsubstituted 1,2-dithiete has been generated in thermolytic reactions and was characterized by microwave spectroscopy, ultraviolet photoelectron spectroscopy and infrared spectroscopy in a low temperature matrix. The open ring isomer, dithioglyoxal, HC(S)C(S)H, is less stable than the 1,2-dithiete.

The dithione can be prepared (as trans-dithioglyoxal) by low temperature photolysis of 1,3-dithiol-2-one. Quantum chemical calculations reproduce the observed greater stability of 1,2-dithiete only if large basis-sets with polarization functions are used.

:[[Image:HONKOK.png|thumb|left|194px|Structure of the dithiete S2C2(CO2Me)2. Selected distances and angles: rC=C = 1.362, rC-S = 1.738, rS-S = 2.072 Å, S-S-C = 78.3°, S-C-S = 102°.]]

Additional reading

References

References

  1. Zoller, U. (1996). "Comprehensive Heterocyclic Chemistry II".
  2. Drabowicz, J. (2008). "Comprehensive Heterocyclic Chemistry III".
  3. (1998). "3,4-Bis(1-adamantyl)-1,2-dithiete: the First Structurally Characterized Dithiete Unsupported by a Ring or Benzenoid Frame". Acta Crystallographica.
  4. (1983). "Theory and application of photoelectron spectroscopy. 100. Variable-temperature photoelectron spectral study of 1,3-dithiol-2-one and 4,5-disubstituted 1,3-dithiol-2-ones. Thermal generation of 1,2-dithiete, 3,4-disubstituted 1,2-dithietes, and dialkyl tetrathiooxalates". Journal of the American Chemical Society.
  5. (6 June 2008). "Infrared detection of dithioglyoxal from photolysis of 1,3-dithiol-2-one in solid argon and nitrogen". Chemical Physics Letters.
  6. (2009). "''Ab initio'' quantum-chemical calculations of the energies and structures of 1,2-acetylenedithiol isomers". Journal of Structural Chemistry.
  7. T. Shimizu. (1998). "Synthesis, Structure, and Ring Conversion of 1,2-Dithiete and Related Compounds". J. Org. Chem..

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organic-disulfidessulfur-heterocyclesfour-membered-rings