Trithiapentalene

Trithiapentalene
Names
	Preferred IUPAC name 7λ4-[1,2]Dithiolo[1,5-b][1,2]dithiole
	Other names 1,6,6aλ4-Trithiapentalene, 6a-Thiothiophthene, 6a-Thiathiophthene
Identifiers
CAS Number	252-09-5;
3D model (JSmol)	Interactive image;
PubChem CID	136064;
UNII	YCW5D22WNB ;
CompTox Dashboard (EPA)	DTXSID80948052 ;
	InChI InChI=1S/C5H4S3/c1-3-6-8-5(1)2-4-7-8/h1-4H Key: JUEJPBZMWHMMPS-UHFFFAOYSA-N;
	SMILES C1=CSS2=C1C=CS2;
Properties
Chemical formula	C5H4S3
Molar mass	160.27 g·mol−1
Appearance	Orange–red solid
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Trithiapentalene is an organic bicyclic molecule containing two sulfur heterocycles. Its 10-π aromatic structure is similar to naphthalene. There has been a literature dispute about whether the connectivity among the three sulfur atoms is a case of rapid tautomerization between two valence tautomers or a 3-center 4-electron bond.^[2]

The reactions have been little studied. It forms a dinickel complex upon reaction with bis(allyl)nickel.^[3]

References

^ Hansen, Lars K.; Hordvik, Asbjørn; Hebrew, C.; Buren, C. T. Van; Klæboe, P.; Swahn, Carl-Gunnar (1973). "The Crystal and Molecular Structure of 6a-Thiathiophthene". Acta Chemica Scandinavica. 27: 411–420. doi:10.3891/acta.chem.scand.27-0411.
^ Pedersen, Carl Th (1991-04-01). "The Structure of Trithiapentalenes and Related Compounds". Phosphorus, Sulfur, and Silicon and the Related Elements. 58 (1–4): 17–38. doi:10.1080/10426509108040624. ISSN 1042-6507.
^ Bogdanović, Borislav; Krüger, Carl; Kuzmin, Oleg (1979). "Bis(η3-allylnickel) 2,4,6-Heptanetrithionediate". Angewandte Chemie International Edition in English. 18 (9): 683–684. doi:10.1002/anie.197906831.