Application of bis(2,2,2-trifluoroethyl) 2-oxoalkylphosphonate reagents made the Horner-Wadsworth-Emmons reactions suitable for the formation of not only E- but Z-unsaturated enones. By this modification, the synthesis of the geometric isomers can be performed by similar reactions. However, preparation of bis(2,2,2-trifluoroethyl) phosphonates by the known methods, raises difficulties. To overcome this challenge, we have previously optimized the reaction parameters for the preparation of these phosphonates. During our work the main impurities were isolated and their structure elucidated. In the present work, we aimed at revealing the mechanisms of these sophisticated chemical transformations using computational methods and experimental results.
- 2,2,2-trifluoroethyl phosphonates
- Horner-Wadsworth-Emmons (HWE) reaction
- mechanistic study
- reaction mechanism
ASJC Scopus subject areas