Mercury, Lewis basicity

The mercuration of ferrocenylimines with Hg(OAc)2 has been studied. - 6 Mercuration occurs selectively at the a-position relative to the imine group to afford compounds 86a-i (Scheme gy107,108 The regioselectivity of these reactions points to the directing role of the Lewis-basic imine functionality. Similar factors probably play a role in the formation of the ferrocenylketone and ferrocenylaldehyde derivatives 87a-f and 87g-j, respectively. These derivatives readily react with amines to afford the corresponding imines (Scheme 9). Presumably, the Lewis-acidic mercury center of the monomercurated ferrocenylketones and ferrocenylaldehydes activates the carbonyl functionality toward nucleophilic attack by the amine. 

The first perfluoroalkykadmium compounds were prepared via metathesis between bis(trifluaromethyl)mercury and dialkylcadmiums [12d] An equilibrium mixture of all possible cadmium and mercury compounds was formed, the equilibrium could be shifted toward the bis(tnfluoromethyl)cadmium by using excess bis(tnflu-oromethyl)mercury When the reaction was earned out in glyme, a stable bis(tnflu-oromethyl)cadmium gly ine complex was isolated [124, 125 126] (equation 96) Other analogues were synthesized and isolated in essentially quantitative yield via direct reaction of primary and secondary perfluoroalkyl iodides with di-alkylcadmiums in basic Lewis solvents [127 128] (equaUon 97)... 

---