Reaction of mercury salts with dimethyl tricyclo [4.2.2.02,5]deca-3,7-diene-cis-endo-9,10-dicarboxylate in acetic acid

Abstract

The reaction of dimethyl tricyclo[4.2.2.02,5]deca-3,7-diene-cis-endo-9,10-dicarboxylate with mercury salts Hg(OCOR)2 (R=CCl3, CF3, CH2Cl) in acetic acid yields a mixture of solvoadducts and products of addition of the anionic moiety of the reagent having thetrans-configuration. In the case of Hg(OCOCCl3)2,cis-solvoadduct was detected along with thetrans-isomer. The amount of the addition products is determined by the nature of the mercury salt and increases in the order Hg(OCOCH2Cl)2<Hg(OCOCCl3)2=Hg(OCOCF3)2. The reaction is assumed to involve contact and solvent-separated ion pairs.