HALOMETHYL-METAL COMPOUNDS .22. PREPARATION OF TRIHALOMETHYL AND OTHER HALOGENATED ORGANOTIN COMPOUNDS

The compounds Me3SnCCl3, Me3SnCCl2H, Me3SnCCl2Ph and Me3SnCCl2-Me have been prepared by reaction of the appropriate organolithium reagent with trimethyltin chloride at low temperature. The reaction of phenyl(bromodichloromethyl)mercury with trimethyltin bromide in refluxing benzene solution produced Me3SnCCl2Br in 63% yield. An experiment in which this mercury reagent was allowed to react with trimethyltin chloride gave both Me3SnCCl3 and Me3SnCCl2Br, which suggests that this route to trihalomethyl-tin compounds proceeds both by CCl2 insertion into the SnX bond and by substituent exchange between mercury and tin. © 1969.