65094-25-9Relevant academic research and scientific papers
A new route to α-fluorovinylphosphonates utilizing Peterson olefination methodology
Waschbuesch, Rachel,Carran, John,Savignac, Philippe
, p. 14199 - 14216 (1996)
Several α-fluorovinylphosphonates (6) have been synthesised from the Peterson olefination reaction applied to both aldehydes and ketones in conjunction with α-lithiated-α-fluoro-α-trimethylsilylmethylphosphonates (2). The reaction with aldehydes gives mainly the E-isomer whereas reaction with ketones gives mainly the Z-isomer. We propose a closed transition state to explain the results of our study.
A New Route to α-Fluoromethyl- and α-Fluoroalkyl-phosphonates
Patois, Carl,Savignac, Philippe
, p. 1711 - 1712 (1993)
α-Fluoroalkylphosphonates are prepared by double-halogen exchange of 1,1,1-dibromofluoroalkylphosphonates with n-butyllithium-trimethylchlorosilane (2:1) followed by alkylation and ethanolysis.
An efficient synthesis of tetraethyl fluoromethylenediphosphonate and derivatives from diethyl dibromofluoromethylphosphonate
Iorga, Bogdan,Eymery, Frederic,Savignac, Philippe
, p. 4477 - 4480 (1998)
Treatment of diethyl 1,1-dibromo-1-fluoromethylphosphonate with n-BuLi (1:1) at low temperature affords by self-trapping in quantitative yield the lithiated derivative of tetraethyl fluoromethylenediphosphonate which is reacted with alkylating and halogenating agents or converted with high selectivity into (E) diethyl fluorovinylphosphonates by reaction with carbonyl compounds.
Synthetic and mechanistic aspects of halo-F-methylphosphonates
Flynn, Richard M.,Burton, Donald J.
experimental part, p. 815 - 828 (2011/10/08)
The synthesis of a variety of new halo-F-methylphosphonates has been achieved by a Michaelis-Arbuzov type reaction between a halo-F-methane and a trialkyl phosphite. This synthesis has proved to be of wide scope and utility for the high yield preparation of a number of heretofore unknown compounds. The 1H, 19F, 13C and 31P NMR spectroscopic properties are reported in detail. The mechanism for the formation of bromodifluoromethylphosphonates has been shown to proceed through the intermediacy of difluorocarbene:CF2. The phosphonate products have been shown to react with a wide variety of reagents. Fluoride and alkoxide ions react by attack at phosphorus with cleavage of the carbon-phosphorus bond and formation of [:CF2] from the bromodifluoromethylphosphonates and the CFBr2- anion from the dibromofluoromethylphosphonates. Iodide ion and tertiary phosphines react by attack at the ester carbon to give stable phosphonate salts. Hydrolysis of the phosphonate esters with 50% aqueous HCl gives the expected phosphonic acids. Trimethylsilyl bromide attacks phosphoryl oxygen to afford the bis(trimethylsilyl) esters.
Preparation of triethyl 2-fluoro-2-phosphonoacetate
Patois,Savignac
, p. 1317 - 1322 (2007/10/02)
Triethyl 2-fluoro-2-phosphonoacetate was prepared in one step from dibromofluoromethyl phosphonate and ethyl chloroformate.
Synthesis of fluorinated phosphonic, sulfonic, and mixed phosphonic/sulfonic acids
Su, Debao,Cen, Wenbiao,Kirchmeier, Robert L.,Shreeve, Jean'ne M.
, p. 1795 - 1799 (2007/10/02)
The acids (HO)2P(O)CFHSO3H, (HO)2P(O)(CF2)4O(CF2)2SO3H, H(CF2)2O(CF2)2P(O)(OH)2, H(CF2)2O(CF2)4P(O)(OH)2, (HO)2P(O)(CF2)2O(CF2)4H, and the acid precursor (C2H5O)2P(O)CF(SO3Na)2 have been synthesized.Elemental analysis, 19F, 1H, and 31P NMR, and mass spectroscopy were used for characterization of these materials.They are very strong acids, and exhibit a high degree of stability in aqueous solution at elevated temperature, which makes them attractive candidates for use as electrolytes in fuel cells.Key words: fluorinated phosphonic acids; fluorinated sulfonic acids; 1H, 19F, 31P NMR.
