Application of fluorocarbethoxy-substituted phosphonate: A facile entry to substituted 2-fluoro-3-oxoesters

Article abstract of DOI:10.1080/10426509708043541

Diethyl(fluorocarbethoxymethyl)phosphonate 1a or diisopropyl(fluorocarbethoxymethyl)phosphonate 1b, prepared from triethyl phosphite or triisopropyl phosphite with ethyl bromofluoroacetate, react with n-butyllithium in THF to give the corresponding phosphonate carbanions [(RO)₂P(O)CFCO₂Et]^-Li⁺ 2a (R = Et) and 2b (R = i-Pr). Addition of trimethylsilyltrifluoroacetate CF₃C(O)OSiMe₃ to a THF solution of phosphonate carbanions formed the enolate of ethyl trifluoroacetylfluoroacetate [CF₃C(O)CFCO₂Et]^-Li⁺ 3. Subsequent protonation, alkylation or allylation of the enolate afforded substituted 2,4,4,4-tetrafluoro-3-oxoesters CF₃C(O)CFR₁CO₂Et 10.

Full text of DOI:10.1080/10426509708043541

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Phosphorus, Sulfur, and Silicon and the
Related Elements
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APPLICATION OF FLUOROCARBETHOXY-
SUBSTITUTED PHOSPHONATE: A FACILE
ENTRY TO SUBSTITUTED 2-FLUORO-3-
OXOESTERS
Hou-Jen Tsai a
a Department of Applied Chemistry , Chung Cheng Institute of
Technology , Ta-Hsi, Tao-Yuan, Taiwan
Published online: 04 Oct 2006.
To cite this article: Hou-Jen Tsai (1997) APPLICATION OF FLUOROCARBETHOXY-SUBSTITUTED
PHOSPHONATE: A FACILE ENTRY TO SUBSTITUTED 2-FLUORO-3-OXOESTERS, Phosphorus, Sulfur, and Silicon
and the Related Elements, 126:1, 1-10, DOI: 10.1080/10426509708043541
To link to this article: http://dx.doi.org/10.1080/10426509708043541
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