Tetrahedron letters

Cyclic mechanism in the trapping of carbonyl oxides with alcohols and carboxylic acids

H Hanaki, Y Fukatsu, M Harada, Y Sawaki

Index: Hanaki, Hiroshi; Fukatsu, Yuta; Harada, Masaki; Sawaki, Yasuhiko Tetrahedron Letters, 2004 , vol. 45, # 12 p. 2559 - 2561

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Citation Number: 2

Abstract

The reaction of diphenylcarbonyl oxide with alcohols and carboxylic acids, which has been classified as a nucleophilic trapping, is shown to be in the reactivity order: AcOH≫ MeOH> CF3CH2OH> EtOH≫ t-BuOH. A laser-flash spectroscopy indicated that the reaction of carboxylic acids is very fast, that is, one-tenth of the diffusion rate. These results suggest that the hydroxyl compounds react as an acid and a nucleophile at the same time and the ...