Title: APPLICATION OF FLUOROCARBETHOXY-SUBSTITUTED PHOSPHONATE: A FACILE ENTRY TO SUBSTITUTED 2-FLUORO-3-OXOESTERS
Abstract: Abstract 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 Key Words: fluorophosphonateMichaelis-Arbuzov reactionenolatealkylationallylation3-oxoesters
Publication Year: 1997
Publication Date: 1997-07-01
Language: en
Type: article
Indexed In: ['crossref']
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Cited By Count: 9
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