1610542-45-4Relevant articles and documents
Diethyl fluoronitromethylphosphonate: Synthesis and application in nucleophilic fluoroalkyl additions
Opekar, Stanislav,Pohl, Radek,Beran, Pavel,Rulisek, Lubomir,Beier, Petr
, p. 1453 - 1458 (2014/04/03)
Diethyl fluoronitromethylphosphonate (3), a previously unknown compound, was synthesized by electrophilic fluorination of diethyl nitromethylphosphonate with Selectfluor. Base-induced decomposition of 3 was studied by NMR spectroscopy, which identified diethyl fluorophosphate and fluoronitromethane as the main decomposition products. C H acidities [pKa values in dimethyl sulfoxide (DMSO)] of 3, 1-fluoro-1-phenylsulfonylmethanephosphonate (1; McCarthy's reagent), tetraethyl fluoromethylenebisphosphonate (2), and some nonfluorinated phosphonates were computed, and a good correlation between calculated and experimental pKa values was found. The calculated C-H acidities increased in the sequence 2a,b-unsaturated carbonyl compounds, sulfones, and nitro compounds allowed access to variously modified diethyl 1-fluoro-1-nitrophosphonates.