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The reactivity of superoxide ion(0₂-) with halogenated substrates is investigated by cyclic voltammetry and rotated ring-disk electrode method in aprotic solvents. The more positive the reduction potential of the substituted nitrile, the more facile is nucleophilic displacement by O₂-. The reaction rates of halogenonitriles with O₂- vary according to the leaving-group propensity of halide (Br＞Cl＞F). The relative reaction rates of other substituted nitriles are in the order of electron-withdrawing propensity of the substituent group (CN＞C(O)NH₂＞Ph, CH₂CN), The reaction of O₂- with dihalocarbons indicates that five-membered rings can be rapidly formed by the cyclization of substrate and O₂- and the relative rates of cyclization depend on the number of methylenic carbons {Br(CH₂)n Br, [n=1＜2＜3＞4＞5]}. Mechanisms are proposed for the reaction of O₂- with halogenated substrates.
목차
Abstract
1. Introduction
2. Experimental
3. Results and Discussion
Acknowledgment
References
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