Add time:07/30/2019         Source:sciencedirect.com

The reaction of phenyl(bromodichloromethyl)mercury-derived dichlorocarbene with bis(trimethylsilyl)mercury in benzene at 80° gave as principal products trimethyl(trichlorovinyl)silane, trimethylchlorosilane, metallic mercury and phenylmercuric bromide. An analogous reaction with bis(trimethylgermyl)mercury gave trimethyl(trichlorovinyl)germane and trimethylchlorogermane. The same reactions were found to occur between phenyl(dibromochloromethyl)- and phenyl(tribromomethyl)mercury and bis(trimethylsilyl)mercury, but the yields of the (trihalovinyl)silanes, Me3SiCClCClBr and Me3SiCBrCBr2 respectively, were much lower. Experimental evidence was gathered which indicated that these reactions proceed via dihalocarbene insertion into the Group IV element-to-mercury bond followed by another CX2 insertion into the newly formed HgC bond in the Me3MCX2Hg intermediate and subsequent β-elimination of HgX from Me3MCX2CX2Hg species thus formed. Among the evidence presented was the finding that the reaction of PhHgCCl2Br-derived dichlorocarbene with Me3SiCCl2Hg compounds gives Me3SiCClCCl2.

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