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

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]

3,4-Bis(trifluoromethyl)-1,2-dithiete
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C4F6S2/c5-3(6,7)1-2(12-11-1)4(8,9)10
    Key: YSIXKKRCABXBLQ-UHFFFAOYSA-N
  • C1(=C(SS1)C(F)(F)F)C(F)(F)F
Properties
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

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
  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.
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