Pentathiepine

Pentathiepine

Identifiers
CAS Number	32711-17-4
3D model (JSmol)	Interactive image
ChemSpider	25946925
PubChem CID	53696760
CompTox Dashboard (EPA)	DTXSID90706024
InChI InChI=1S/C2H2S5/c1-2-4-6-7-5-3-1/h1-2H Key: BRCAXRYKWZIFOK-UHFFFAOYSA-N
SMILES 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). Infobox references

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

C₆H₄(SH)₂ + 0.5 S₈ → C₆H₄(S₅) + H₂S

Related compounds

Varacin is a naturally-occurring pentathiepine

Substituted benzopentathiepines occur naturally in the form of varacin and the lissoclinotoxins. ^[3]

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.