Kinetic measurements of the reaction among eight substituted benzaldehydes and ethylene oxide in the presence of catalytic amounts of tetrabutylammonium halides have been performed. With poor electrophilic aldehydes the rate-determining step of the reaction is the nucleophilic attack of the halogeno ethoxide anion to the carbonyl group while with rich electrophilic aldehydes the rate-determining step becomes the ring opening of ethylene oxide by the halide ion. Hammett correlations and kinetic results confirm these proposed mechanisms.
|Journal||Journal of the Chemical Society, Perkin Transactions 2|
|Publication status||Published - 1 Jan 1986|
Font, J., Galán, M. A., & Virgili, A. (1986). Kinetics and mechanism of 1,3-dioxolane formation from substituted benzaldehydes with ethylene oxide in the presence of tetrabutylammonium halides. Journal of the Chemical Society, Perkin Transactions 2, (1), 75-78. https://doi.org/10.1039/P29860000075