Mechanistic Study on the Acylation ofBis(2,2,2-Trifluoroethyl) Methylphosphonate by Carboxylic Esters

Katalin Molnár, László Takács, Zoltán Mucsi, F. Faigl, Zsuzsanna Kardos

Research output: Contribution to journalArticle

Abstract

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.

Original languageEnglish
Pages (from-to)7723-7734
Number of pages12
JournalChemistrySelect
Volume2
Issue number25
DOIs
Publication statusPublished - Jan 1 2017

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Acylation
Organophosphonates
Esters
Computational methods
Isomers
Impurities
methylphosphonic acid

Keywords

  • 2,2,2-trifluoroethyl phosphonates
  • Horner-Wadsworth-Emmons (HWE) reaction
  • mechanistic study
  • reaction mechanism

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Mechanistic Study on the Acylation ofBis(2,2,2-Trifluoroethyl) Methylphosphonate by Carboxylic Esters. / Molnár, Katalin; Takács, László; Mucsi, Zoltán; Faigl, F.; Kardos, Zsuzsanna.

In: ChemistrySelect, Vol. 2, No. 25, 01.01.2017, p. 7723-7734.

Research output: Contribution to journalArticle

Molnár, Katalin ; Takács, László ; Mucsi, Zoltán ; Faigl, F. ; Kardos, Zsuzsanna. / Mechanistic Study on the Acylation ofBis(2,2,2-Trifluoroethyl) Methylphosphonate by Carboxylic Esters. In: ChemistrySelect. 2017 ; Vol. 2, No. 25. pp. 7723-7734.
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