691889-72-2Relevant articles and documents
Cyclic mechanism in the trapping of carbonyl oxides with alcohols and carboxylic acids
Hanaki, Hiroshi,Fukatsu, Yuta,Harada, Masaki,Sawaki, Yasuhiko
, p. 2559 - 2561 (2004)
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?MeOHCF3CH2OHEtOH?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.