Halomethyl-metal compounds VI. Phenyl(dihalomethyl)mercury compounds: Their preparation and some cleavage reactions

Abstract

Phenyl(dibromomethyl)mercury, phenyl(bromochloromethyl)mercury, phenyl(dichloromethyl)mercury, phenyl(bromoiodomethyl)mercury, phenyl(chloroiodomethyl)mercury and phenyl(diiodomethyl)mercury have been prepared by the reaction of phenylmercuric chloride with the appropriate dihalomethane and potassium tert-butoxide in toluene solution. Phenyl(chloroiodomethyl)mercury, is more readily accessible by the reaction of phenyl(bromochloromethyl)mercury with one molar equivalent of sodium iodide in methanol/benzene medium. The action of an excess of sodium iodide on C 6H 5HgCHX 2. (X = Cl or Br) resulted in formation oi phenyl(diiodomethyl)mercury. Methanolic hydrogen bromide and bromine in carbon tetrachloride cleave first a phenyl group from phenyl(dihalomethyl)mercurials, giving CHX 2HgBr compounds, but an excess of these reagents causes complete cleavage of organic groups from mercury. The IR and NMR spectra of these mercurials are presented and their significant feature are discussed.