Electroactive Protecting Groups and Reaction Units. Part 1. Mesolytic Cleavage of the O-CO Bond in Enol Acetate Cation Radicals with Direct Formation of. alpha.- …

M Schmittel, J Heinze, H Trenkle

Index: Schmittel, Michael; Heinze, Juergen; Trenkle, Holger Journal of Organic Chemistry, 1995 , vol. 60, # 9 p. 2726 - 2733

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Abstract

For the first time, enol ester cation radicals are reversibly monitored in a cyclic voltammetry experiment. Preparative one-electron oxidation of enol acetates A1-A4 leads to the formation of benzofurans Bl-B4 through mesolytic 0-CO bond fragmentation to a-carbonyl cations and the acetyl radical. With A3*+, the kinetics of the 0-CO bond cleavage was investigated by cyclic voltammetry, providing AP= 17.0 kcal mol-'and AS*= 11 cal mol-l K-' ...