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, because the products are particularly easy to extract from the reaction mixture. Strong nucleophiles may catalyze the reaction by displacing CCl−3 from mercury, although the free ion is not believed to form in the process. Unusually, the pure organomercury compound reacts with electron-poor alkenes, converting tetrachloroethylene to 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.
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