Tetrachlorocyclopropene Explained

Tetrachlorocyclopropene is a chemical compound with the formula C₃Cl₄. A colorless liquid, the compound is a reagent used to prepare acetylene derivatives and in organic synthesis.^[1] It is prepared by addition of dichlorocarbene to trichloroethylene.^[2] It can react with water and alcohols rapidly.^[3]

The compound is used to prepare arylpropiolic acids:

C₃Cl₄ + ArH + 2 H₂O → ArC₂CO₂H + 4 HCl

Under some circumstances, diarylation occurs, giving diarylcyclopropenones, which decarbonylate to give diarylacetylenes. These reactions are thought to proceed via the intermediacy of trichlorocyclopropenium electrophile (C₃Cl₃⁺).

References

1. Tetrachlorocyclopropene. Oliver Reiser . Armin de Meijere . EEROS. 2001. 10.1002/047084289X.rt028. 0-471-93623-5 .
2. Glück. C. Poingée. V. Schwager. H. Improved Synthesis of 7,7-Difluorocyclopropabenzene. Synthesis. 1987. 3. 1987. 260–262. 10.1055/s-1987-27908. 96607067.
3. Pentachlorocyclopropane Stephen W. Tobey and Robert West. The University of Wisconsin (1965)