ChemInform Abstract: PERFLUOROALKYL PHOSPHONOUS ACID ESTERS

Maslennikov, I. G.; Lavrent'ev, A. N.; Khovanskaya, N. V.; Lebedev, V. B.; Sochilin, E. G.

doi:10.1002/chin.197950275

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2011

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“…In addition, direct hydrolysis of the isolated iodides results in trace iodine contamination. This issue can be circumvented on a small scale by metathesis of the iodides to chlorides; however, stoichiometric AgCl or SbCl 3 are required. , Ultimately these methods lead to maximum overall yields of the final perfluoroalkylphosphonic acid of 30% or less based on the corresponding perfluoroalkyl iodide.…”

Section: Introductionmentioning

confidence: 99%

Reaction of Perfluoroalkyl Grignard Reagents with Phosphorus Trihalides: A New Route to Perfluoroalkyl-phosphonous and -phosphonic Acids

et al. 2011

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The reaction of perfluoroalkyl Grignard reagents with phosphorus(III) halides was explored. In the process a new convenient, one-pot, high yield method for the synthesis of (perfluoroalkyl)phosphonic acids has been developed. Perfluoroalkyl Grignard reagents react with phosphorus trichloride or phosphorus tribromide to form (perfluoroalkyl)phosphonous dihalides. Hydrolysis gives the corresponding (perfluoroalkyl)phosphonous acids. Oxidation of the phosphonous acids with H(2)O(2) produces (perfluoroalkyl)phosphonic acids in 60-78% overall yields, based on the corresponding perfluoroalkyl iodide. The X-ray crystal structures of the toluidinium salts, [MeC(6)H(4)NH(3)](2)[C(2)F(5)PO(3)] and [MeC(6)H(4)NH(3)][C(8)F(17)P(O)(2)OH], are reported.

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Section: Introductionmentioning

confidence: 99%