3,4-Bis(trifluoromethyl)-1,2-dithiete

3,4-Bis(trifluoromethyl)-1,2-dithiete
Identifiers
CAS Number	360-91-8 ;
3D model (JSmol)	Interactive image;
ChemSpider	119970;
PubChem CID	136194;
CompTox Dashboard (EPA)	DTXSID60189562 ;
	InChI InChI=1S/C4F6S2/c5-3(6,7)1-2(12-11-1)4(8,9)10 Key: YSIXKKRCABXBLQ-UHFFFAOYSA-N;
	SMILES C1(=C(SS1)C(F)(F)F)C(F)(F)F;
Properties
Chemical formula	C4F6S2
Molar mass	226.15 g·mol−1
Appearance	yellow liquid
Boiling point	96 °C (205 °F; 369 K)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

3,4-Bis(trifluoromethyl)-1,2-dithiete is the organofluorine compound with the formula (CF₃)₂C₂S₂, a yellow liquid. It is a stable 1,2-dithiete. It arises by the reaction of hexafluoro-2-butyne with molten sulfur.^[1]

Bonding

Being planar with six pi-electrons, the compound is considered to be aromatic. This description is supported by an electron diffraction study,^[2] which reveals an elongated C=C distance of 1.40 Å and shortened C-S distances of 1.73 Å.

Reactions

The compound tends to dimerize at room temperature, but the dimer cracks at higher temperature back to the dithiete. It is used to prepare metal dithiolene complexes. It reacts with low valent metal complexes by oxidative addition:^[3]

Ni(CO)₄ + 2 (CF₃)₂C₂S₂ → Ni(S₂C₂(CF₃)₂)₂ + 4 CO

Mo(CO)₆ + 3 (CF₃)₂C₂S₂ → Mo(S₂C₂(CF₃)₂)₃ + 6 CO

References

^ Krespan, C. G.; McKusick, B. C.; Cairns, T. L. (1960). "Dithietene and Bicycloöctatriene Ring Systems from Bis-(Fluoroalkyl)-Acetylenes". Journal of the American Chemical Society. 82 (6): 1515–1516. doi:10.1021/ja01491a072.
^ Hencher, J. Lawrence; Shen, Quang; Tuck, Dennis G. (1976). "Molecular Structure of 1,2-Bis(trifluoromethyl)dithiete by Vapor Phase Electron Diffraction". Journal of the American Chemical Society. 98 (4): 899–902. doi:10.1021/ja00420a006.
^ Davison, A.; Holm, R. H.; Benson, R. E.; Mahler, W. (2007). "Metal Complexes Derived from cis-1,2-Dicyano-1,2-ethylenedithiolate and Bis(Trifluoromethyl)-1,2-dithiete". Inorganic Syntheses. pp. 8–26. doi:10.1002/9780470132418.ch3. ISBN 9780470132418.

[1] Krespan, C. G.; McKusick, B. C.; Cairns, T. L. (1960). "Dithietene and Bicycloöctatriene Ring Systems from Bis-(Fluoroalkyl)-Acetylenes". Journal of the American Chemical Society. 82 (6): 1515–1516. doi:10.1021/ja01491a072.

[2] Hencher, J. Lawrence; Shen, Quang; Tuck, Dennis G. (1976). "Molecular Structure of 1,2-Bis(trifluoromethyl)dithiete by Vapor Phase Electron Diffraction". Journal of the American Chemical Society. 98 (4): 899–902. doi:10.1021/ja00420a006.

[3] Davison, A.; Holm, R. H.; Benson, R. E.; Mahler, W. (2007). "Metal Complexes Derived from cis-1,2-Dicyano-1,2-ethylenedithiolate and Bis(Trifluoromethyl)-1,2-dithiete". Inorganic Syntheses. pp. 8–26. doi:10.1002/9780470132418.ch3. ISBN 9780470132418.

[1]

[2]

[3]