Abstract
3, 4-Epoxy-3-methyl-1-butene was obtained from the reaction of isoprene with perbenzoic acid (PBA).
The rate constants of this epoxidation were measured in various solvents at -18°C, -14°C -10°C and -6°C, and the several kinetic parameters were calculated (Table 1). The solvent order with decreasing rate constants was as follows; chloroform>1, 2-dichloroethane>chloro-benzene>toluene>carbon tetrachloride. This is the same order as that of epoxidation of butadiene.
A close correlation was found between the rates of epoxidation and the polarographic half-wave potentials of PBA in some mixed solvent system (Table 2). Further, the rate of hydrogen-deuterium interchange of PBA in various solvents was measured by NMR, and gives greater values in oxygen-contaning solvents (Figure 2). A good correlation was observed between the rate of epoxidation and the basicity of solvents; generally, the increas-ing basicity of solvents results in the decreasing rate of epoxidation reaction.
