Phenyl(trichloromethyl)mercury is an organomercury compound with the formula C6H5HgCCl3. It is a white solid that is soluble in organic solvents. The compound is used as a source of dichlorocarbene, e.g. in cyclopropanation reactions, illustrated with tetrachloroethylene as a substrate, the product being hexachlorocyclopropane: C6H5HgCCl3 → C6H5HgCl + CCl2 CCl2 + Cl2C=CCl2 → C3Cl6
The compound is prepared by treating phenylmercuric chloride with sources of dichlorocarbene. These include the base/haloform reaction and thermolysis of sodium trichloroacetate: NaO2CCCl3 + C6H5HgCl → C6H5HgCCl3 + NaCl + CO2
Related compounds
Closely related compounds include phenyl(bromodichloromethyl)mercury (CAS registry number 3294-58-4) and phenyl(tribromomethyl)mercury (CAS registry number 3294-60-8). According to X-ray crystallography, the former has nearly linear coordination geometry at mercury, with a C-Hg-C angle of 179° and Hg-C distances of 2.047 Å.
Also known is bis(trichloromethyl)mercury, Hg(CCl3)2.