Cyclic mechanism in the trapping of carbonyl oxides with alcohols and carboxylic acids |
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| Authors: | Hiroshi Hanaki |
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| Affiliation: | Department of Applied Chemistry, Graduate School of Engineering, Nagoya University, Chikusa-ku, Nagoya 464-8603, Japan |
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| 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 major reaction is via the seven- and five-membered cyclic mechanism for RCO2H and ROH, respectively. |
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| Keywords: | Carbonyl oxides Cycloadditions Alcohols Carboxylic acids and derivatives Peroxides Mechanisms |
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