Solvomercuration-Demercuration. 11. Alkoxymercuration-Demercuration of Representative Alkenes in Alcohol Solvents with the Mercuric Salts Acetate, Trifluoroacetate, Nitrate, and Methanesulfonate

The alkoxymercuration-demercuration of seven representative olefins with the mercuric salts acetate, trifluoroacetate, nitrate, and methanesulfonate, in methyl, ethyl, isopropyl, and tert-butyl alcohols was examined. Mercuric acetate was effective only in methanol and ethanol. On the other hand, mercuric trifluoroacetate was effective in all four solvents, giving in most cases high yields of the corresponding ethers. Both mercuric nitrate and mercuric methanesulfonate were effective in methanol, ethanol, and 2-propanol. However, in several cases poor selectivity for the ether was observed, as evidenced by the formation of significant amounts of side products. Both electronic and steric effects are important factors in the reaction. Moreover, the structure of the olefin has a pronounced effect, both on the types of oxymercurials formed and on their stability to the reaction conditions.