A STUDY OF THE EFFECT OF SUBSTITUENTS AND OF SOLVENT ON THE REACTIVITY OF THE NORMAL AND ABNORMAL POSITIONS OF UNSYMMETRICAL ORGANIC EPOXIDES
SOUTHAMPTON UNIV (ENGLAND)
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An investigation was made on the reactivity of the normal and abnormal positions of unsymmetrical epoxides. The studies were concerned with the reaction kinetics of 6 m - and p - substituted styrene oxides with benzylamine in ethanol. Results showed that the rate of the normal reaction is increased by electron-withdrawing substituents and decreased by electron-releasing substituents, while the rate of the abnormal reaction is decreased by electron-withdrawing substituents and increased by electron-releasing substitue. Analysis of solvent effect on the reactivity of the normal and abnormal p sitions of unsymmetrical epoxides indicated that alcohols exert a specific accelerating effect which was attributed to H bonding between the alcoholic hydroxyl group and the epoxide oxygen atom. Within the alcohol series the rates of the normal and abnormal reactions increase with dielectric constant in an approximate linear manner.