Kinetic study of the methanolysis of two dibromocyclopropanes: second-order catalysis by silver ion

Abstract

The silver ion-assisted methanolyses of 9,9-dibromobicyclo[6.1.0]nonane (1) and 9,9-dibromobicyclo-[6.1.0]non-4-ene (2) show both first- and second-order dependence on silver(I) ion; the rate of methanolysis of the olefinic substrate (2) is an order of magnitude greater than that of (1) while for both substrates the ratios of rate constants first- and second-order in silver are close to 1 : 10.