Thianthrene

Thianthrene

Thianthrene

Chemical compound

Thianthrene is a sulfur-containing heterocyclic chemical compound. It is a derivative of the parent heterocycle called dithiin. It is notable for its ease of oxidation.

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Structure and synthesis

Like other 1,4-dithiins but unlike its oxygen analog dibenzodioxin, the shape of thianthrene is not planar. It is bent, with a fold angle of 128° between the two benzo groups.[3][4][5]

Thianthrene can be prepared by treating benzene with disulfur dichloride in the presence of aluminium chloride.[6]

History

Thianthrene was first synthesized by John Stenhouse by dry distillation of sodium benzenesulfonate.[7] Thianthrene is oxidized by sulfuric acid forming a red radical cation.[8] Thianthrene•+ has been characterized by Electron paramagnetic resonance. Four different publications describe the crystal structure of salts of thianthrene•+.[9]

References

  1. [1]
    International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 216. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. [2]
    Thianthrene at Sigma-Aldrich
  3. [3]
    Hosoya, S. (1963). "Molecular shapes of thianthrene and related heterocyclic compounds". Acta Crystallographica. 16 (4): 310–312. Bibcode:1963AcCry..16..310H. doi:10.1107/S0365110X63000797.
  4. [4]
    Gallaher, K. L.; Bauer, S. H. (1975). "Structure and inversion potential of thianthren". Journal of the Chemical Society, Faraday Transactions 2. 71: 1173–1182. doi:10.1039/F29757101173.
  5. [5]
    Aroney, M. J.; Le Fèvre, R. J. W.; Saxby, J. D. (1965). "92. Molecular polarisability. The apparent conformations of thianthren and of three of its oxides as solutes in benzene". Journal of the Chemical Society (Resumed): 571–575. doi:10.1039/JR9650000571.
  6. [6]
    US patent 3997560, "Process for the manufacture of thianthrene", issued 1976-12-14.
  7. [7]
    Stenhouse, J. (1869). "Ueber die Producte der trockenen Destillation der sulfobenzolsauren Salze" [On the Dry Distillation Products from Sulfobenzoic Acid Salts]. Annalen der Chemie und Pharmacie (in German). 149 (2): 247–255. doi:10.1002/jlac.18691490216.
  8. [8]
    W. Dilthey: Versammlungsberichte Bonner Chemische Gesellschaft, Angewandte Chemie, Volume 42, Issue 24, pp. 668–670, 15. June 1929; doi:10.1002/ange.19290422405.
  9. [9]
    Shine, Henry J. (July 1998). "EPR and the History of the Thianthrene Cation Radical". Foundations of modern EPR. World Scientific. ISBN 978-981-02-3295-5.
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