Synthesis of α-fluorinated phosphonoacetate derivatives using electrophilic fluorine reagents: Perchloryl fluoride versus 1-chloromethyl-4-fluoro-1, 4-diazoniabicyclo [ …

…, V Harutunian, BA Kashemirov, CE McKenna

Index: Marma, Mong S.; Khawli, Leslie A.; Harutunian, Vahak; Kashemirov, Boris A.; McKenna, Charles E. Journal of Fluorine Chemistry, 2005 , vol. 126, # 11-12 p. 1467 - 1475

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Citation Number: 22

Abstract

Triethyl fluorophosphonoacetate and triethyl difluorophosphonoacetate are directly synthesized from triethyl phosphonoacetate by treatment with NaH and 1-chloromethyl-4- fluoro-1, 4-diazoniabicyclo [2.2. 2] octane bis (tetrafluoroborate)(Selectfluor®). Contrary to a recent report [CJ Hamilton, SM Roberts, J. Chem. Soc., Perkin Trans. 1 (1999) 1051–1056], the reaction proceeded in THF without the need for DMF as a co-solvent. This method is ...