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Dithiete

Dithiacyclobutene 1,2-Dithia[4]annulene

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-disulfides sulfur-heterocycles four-membered-rings
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