Pentathiepine

Pentathiepine
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C2H2S5/c1-2-4-6-7-5-3-1/h1-2H
    Key: BRCAXRYKWZIFOK-UHFFFAOYSA-N
  • C1=CSSSSS1
Properties
Appearance pale yellow solid
Related compounds
Related compounds
 Pentathiepane, tetrathiepine, 1,2,5-Trithiepane
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pentathiepine is an organosulfur compound and sulfur heterocycle with the formula (CH)2S5. Many derivatives are known, often with a benzo group (C6H4) in place of the alkene. Such compounds are derivatives of 1,2-benzenedithiol:

C6H4(SH)2 + 0.5 S8 → C6H4(S5) + H2S
Varacin is a naturally-occurring pentathiepine

Substituted benzopentathiepines occur naturally in the form of varacin and the lissoclinotoxins.

References

  1. ↑ Konstantinova, Lidia S.; Amelichev, Stanislav A.; Rakitin, Oleg A. (2007). "1,2,3,4,5-Pentathiepines and 1,2,3,4,5-pentathiepanes". Russian Chemical Reviews. 76 (3): 195–211. Bibcode:2007RuCRv..76..195K. doi:10.1070/RC2007v076n03ABEH003676.
  2. ↑ Behar V, Danishefsky SJ (1993-07-01). "Total synthesis of the novel benzopentathiepin varacinium trifluoroacetate: the viability of "varacin-free base"". Journal of the American Chemical Society. 115 (15): 7017–7018. Bibcode:1993JAChS.115.7017B. doi:10.1021/ja00068a087. ISSN 0002-7863.
  3. ↑ Searle, Philip A.; Molinski, Tadeusz F. (1994). "Five new alkaloids from the tropical ascidian, Lissoclinum sp. Lissoclinotoxin a is chiral". The Journal of Organic Chemistry. 59 (22): 6600–6605. doi:10.1021/jo00101a018.