James M. Burlitch

Halomethyl-metal compounds : I. Preparation of phenyl(trihalomethyl)mercury compounds

Abstract Detailed procedures for the preparation of C 6 H 5 HgCCl 3 , C 6 H 5 HgCCl 2 Br, C 6 H 5 HgCClBr 2 and C 6 H 5 HgCBr 3 by the Reutov-Lovtsova method are given. Evidence is presented which indicates that the reaction of phenylmercuric halide, haloform and potassium tert -butoxide forms C 6 H 5 HgCX 3 by way of nucleophilic displacement of halide ions from mercury by the trihalomethyl anion.

Halomethyl-metal compounds X. The reaction of organosilicon, organogermanium and organotin hydrides with phenyl(trihalomethyl)mercury compounds☆

Abstract The reaction of phenyl(trihalomethyl)mercury compounds, C6H5HgCX2Br (X=Cl and Br), with organosilicon and organogermanium hydrides in benzene at 80° results in insertion of CCl2 and CBr2, respectively, into the Si—H and Ge—H bonds to give Si—CX2H and Ge—CX2H compounds. Triethylgermane was found to be four times more reactive than triethylsilane, and triethylsilane was 0.8 times as reactivate as cyclohexene. Evidence was obtained which suggest that dihalocarbenes (free or complexed) are involved as intermediates in these reactions. Tri-n-butyltin hydride reduced the C-Br bond of C6H5HgCX2Br mercurials, and C6H5HgCCl2H, C6H5HgCClBrH and C6H5HgCBr2H were prepared and characterized. However, this is not a practical preparative route to these mercurials.