MERCURY SALT CATALYZED NITRATION OF BENZENE-DERIVATIVES

The isomer distributions and product yields have been determined for the mercuric acetate catalyzed nitration of 1, 2- and 1, 3-dimethylbenzenes, 1, 1'-biphenyl, (l, l-dimethylethyl)benzene, the halobenzenes, and methoxybenzene. In most instances, the mercury salt catalyzed reaction exerts a strong influence on the reaction rate and on the product distribution. The isomer distributions are effectively controlled in the reactions of the hydrocarbons. Moreover, the side-chain substitution and ipso reaction products are suppressed in the catalyzed nitration of 1, 2-dimethylbenzene. The halobenzenes undergo mercury(II)-catalyzed nitration, but the reactions are slow. The nitration of the mercurated methoxybenzenes produces 15% 2- and 85% 4-nitromethoxybenzene in 90% yield. However, the catalytic reaction has not been successfully accomplished. All the experimental results are in accord with the view that the mercuration reaction is the rate- and product-determining process in this nitration reaction. © 1979, American Chemical Society. All rights reserved.