Synthesis of new α,α,β,β-tetrafluoroesters

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Substituted phenyl iodides or diiodides reacted with ethyl iodotetrafluoroproponylate ICF2CF2CO2 Et, 1 in the presence of copper powder to give the coupled products 2 or 3 in good yields. Addition of 1 to ethylene and allyl acetate proceeded smoothly under thermal and radical conditions to give the corresponding adducts, which underwent elimination reaction to give β-vinyl and β-allyl α,α,β ,β-tetrafluoroesters, CH2-CHCF2 CF2CO2Et, 4 and CH2=CHCH2CF2CF2 CO2Et, 5, respectively. 1 also readily reacted with 1,5-hexadiene and 1-hexene with copper or palladium complex, followed by reduction to remove iodine to produce ω-alkenyl-α,α,β,β-tetrafluoroester CH2=CH(CH2)4CF2 CF2CO2Et 6 and α,α,β, β-tetrafluoroester C4H9CH2 CHICF2CF2CO2Et. © 2004 Elsevier B.V. All rights reserved.




Yang, Z. Y. (2004). Synthesis of new α,α,β,β-tetrafluoroesters. Journal of Fluorine Chemistry, 125(5), 763–765.

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