Chemistry:Pentathiepine

From HandWiki

Pentathiepine is an organosulfur compound and sulfur heterocycle with the formula (CH)
2
S
5
.[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]

C
6
H
4
(SH)
2
+ 0.5 S
8
→ C
6
H
4
(S
5
) + H
2
S
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. doi:10.1070/RC2007v076n03ABEH003676. Bibcode2007RuCRv..76..195K. 
  2. "Total synthesis of the novel benzopentathiepin varacinium trifluoroacetate: the viability of "varacin-free base"". Journal of the American Chemical Society 115 (15): 7017–7018. 1993-07-01. doi:10.1021/ja00068a087. ISSN 0002-7863. Bibcode1993JAChS.115.7017B. 
  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.