Rate Constants for Electron Transfer and Radical Cation Reactions of Methylated Naphthalenes

Abstract

Since kinetic measurements of base-promoted arene oxidations by tris(phenanthroline)iron(III) provide a ready method for determining rate constants for both electron transfer (ET) and follow-up reactions of arene radical cation intermediates, [1–3] we are using this approach to study the effects of structure on the reactions of radical cations, especially the competition between side chain fragmentation and nucleophilic addition reactions. In this paper, we report our findings for methylated naphthalenes and make comparisons with data for methylated benzenes that were reported by Kochi, Amatore and Schlesener [1].