2- fluoro-2-phosphonoacetate, triethyl

Machleidt reported the Homer-Emmons reaction of triethyl-fluoro-phosphonoacetate with aldehydes and ketones to give a-fluoro-a,p-unsaturated esters (entry 2) (76). In the case of aldehydes the reaction is highly E-selective (77), a property which was used for the preparation of fluorinated pheromones (18) and 5-fluoro-arachidonic acid (79). 

There do not appear to be any simple phosphines that bear a CH2F group. However, fluorine NMR spectra of phosphonates, phosphane oxides, and phosphonium compounds with CH2F and —CHF- bound to phosphorous have been reported. Examples are given in Scheme 3.26, including spectral data for the useful Horner-Wadsworth-Emmons reagent, triethyl 2-fluoro-2-phosphonoacetate. 

Patois, C., and Savignac, P, Preparation of triethyl 2-fluoro-2-phosphonoacetate, Synth. Commun., 24, 1317, 1994. 

Kim, D.Y., Choi, J.S., and Rhie, D.Y., P-C bond cleavage of triethyl 2-fluoro-3-oxo-2-phosphonoacetates with magnesinm chloride. A synthesis of a-fluoro-P-keto esters, Synth. Commun., Tl, 1097, 1997. 

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