Ketene-diene [4+ 2] cycloaddition products via cation radical initiated Diels-Alder reaction or vinylcyclobutanone rearrangement

M Schmittel, H Von Seggern

Index: Schmittel, Michael; Von Seggern, Heinke Journal of the American Chemical Society, 1993 , vol. 115, # 6 p. 2165 - 2177

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Citation Number: 2

Abstract

Abstract: Whereas the thermal reaction of the aryl methyl ketenes la and lb with 2 resulted, as anticipated, in the periselective formation of the vinylcyclobutanones 3-6, the aminium ion salt initiated cycloaddition afforded selectively the Diels-Alder products 10 and 12. The potential role of Bronsted and Lewis acids, the suitability of different one-electron oxidants, and the effect of reactant concentration, reaction time, and added neutral amines was ...