1138-99-4Relevant articles and documents
Fraser et al.
, p. 1455 (1972)
Smith
, p. 6176 (1960)
Deoxygenative Fluorination of Phosphine Oxides: A General Route to Fluorinated Organophosphorus(V) Compounds and Beyond
Bornemann, Dustin,Brüning, Fabian,Grützmacher, Hansj?rg,Guan, Liangyu,Küng, Sebastian,Pitts, Cody Ross,Togni, Antonio,Trapp, Nils,Wettstein, Lionel
supporting information, p. 22790 - 22795 (2020/10/06)
Fluorinated organophosphorus(V) compounds are a very versatile class of compounds, but the synthetic methods available to make them bear the disadvantages of 1) occasional handling of toxic or pyrophoric PIII starting materials and 2) a dependence on hazardous fluorinating reagents such as XeF2. Herein, we present a simple solution and introduce a deoxygenative fluorination (DOF) approach that utilizes easy-to-handle phosphine oxides as starting materials and effectively replaces harsh fluorinating reagents by a combination of oxalyl chloride and potassium fluoride. The reaction has proven to be general, as R3PF2, R2PF3, and RPF4 compounds (as well as various cations and anions derived from these) are accessible in good yields and on up to a multi-gram scale. DFT calculations were used to bolster our observations. Notably, the discovery of this new method led to a convenient synthesis of 1) new difluorophosphonium ions, 2) hexafluorophosphate salts, and 3) fluorinated antimony- and arsenic- compounds.
Triphenylmethyl fluoride as a fluorinating agent in phosphorus-halogen chemistry
Plack, Volker,Goerlich, Jens R.,Schmutzler, Reinhard
, p. 173 - 176 (2007/10/03)
Triphenylmethyl fluoride 1 will effect chlorine-fluorine exchange in certain phosphorus chlorides. Exchange of chlorine for fluorine was observed only in σ3λ3 (P)- and σ5λ5 (P)-compounds, while phosphorus oxychloride as an example of a σ4λ5 (P)-compound was unreactive towards 1.
FLUORINATION OF DERIVATIVES OF TRI- AND PENTAVALENT PHOSPHORUS ACIDS BY PERFLUOROPROPYLENE OXIDE
Lermontov, S. A.,Rakov, I. M.,Martynov, I. V.
, p. 2584 - 2587 (2007/10/02)
Perfluoropropylene (I) efficiently fluorinates esters and ester anhydrides of PIII and PV acids to give acid fluoride derivatives of pentavalent phosphorus acids.Phosphites are initially oxidized to the corresponding phosphoryl compounds with subsequent substitution of the oxygen by two fluorine atoms by means of excess oxide (I).
