Abstract
The synthesis and electrochemical investigation of six stable, simple enols E1-E6 are reported that are characterized by electron-releasing substituents in the alpha-position. Oxidative benzofuran formation from these enols is unusually slow because a key intermediate in the reaction, the dihydrobenzofuranyl cation X(+), is substantially stabilized vs rearrangement by the attached electron-releasing substituents. The persistent cations X(+) were characterized by (1)H NMR and cyclic voltammetry, and the kinetics of their rearrangement was followed by UV/vis. Notably, upon one-electron oxidation of X(+) to the radical dication, the formation of the benzofurans B was markedly accelerated by a factor of >10(6).
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