Halomethyl-metal compounds. LXXIX. The generation of isopropylidene carbene by the organomercury route

Article abstract of DOI:10.1016/S0022-328X(00)91663-2

Bis(1-bromo-2-methylpropenyl)mercury, prepared via Me₂CC(Br)Li, was treated with mercuric bromide to give Me₂CC(Br)HgBr. The latter transferred Me₂CC: to olefins, giving isopropylidenecyclopropanes, in sealed tube reactions carried out at 150°C in the presence of an equimolar quantity of diphenylmercury. The Me₂CC(Br)HgBr/Ph₂Hg reagent also reacted with triethylsilane at 150°C to give Et₃SiCHCMe₂ in nearly quantitative yield.