Synthesis and Characterization of Some Perfluorophenylphosphine Derivatives

Magnelli, D. D.; Tesi, Godswill O.; Lowe, James U.; McQuistion, William E.

doi:10.1021/ic50037a027

Cited by 45 publications

(27 citation statements)

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“…[6] The bis(trifluoromethyl)phosphinous acid (CF 3 ) 2 POH, synthesized in 1960 by Griffiths and Burg, [7,8,9] represents to date the only known example of a diorganylphosphinous acid. The compound with the composition (C 6 F 5 ) 2 POH originally claimed [10] as bis(pentafluorophenyl)phosphinous acid has been shown to exist both in the solid state and in solutions of CHCl 3 , toluene, or diethyl ether exclusively in the phosphane oxide form. The phosphinous acid can be detected by NMR spectroscopic methods only in solvents with high donor numbers.…”

Section: Introductionmentioning

confidence: 99%

The Bis(pentafluoroethyl)phosphinous Acid (C₂F₅)₂POH

Hoge¹,

Bader²,

Beckers³

et al. 2009

Chemistry A European J

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The industrial product (C(2)F(5))(3)PF(2) is transformed into the phosphinic acid chloride (C(2)F(5))(2)P(O)Cl, which reacts with an excess of Bu(3)SnH in a clean, multistep reaction to give the stannyl derivative (C(2)F(5))(2)POSnBu(3). Subsequent treatment with gaseous HBr leads to the formation of (C(2)F(5))(2)POH, which is isolated in 70 % yield. Besides (CF(3))(2)POH, bis(pentafluoroethyl)phosphinous acid, (C(2)F(5))(2)POH, represents the second known example of a phosphinous acid that is predicted by using density functional theory calculations at the B3PW91/6-311G(3d,p) level to be more stable than the phosphane oxide tautomer, the energy difference being 11.7 kJ mol(-1). Only the phosphinous acid isomer is detectable in the gas phase and in solution. However, investigations of the neat liquid reveal a temperature-dependent tautomeric equilibrium with the phosphane oxide isomer (C(2)F(5))(2)P(O)H, which is characterized by vibrational and multinuclear NMR spectroscopic methods in combination with quantum-chemical calculations.

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Section: Introductionmentioning

confidence: 99%

The Bis(pentafluoroethyl)phosphinous Acid (C₂F₅)₂POH

Hoge¹,

Bader²,

Beckers³

et al. 2009

Chemistry A European J

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“…sized as described by Magnelli and co-workers (17). To lithium propynylide (0.1 mol) in etherlhexane 1 :1 at -78" (from CH,C=CH + 12-C4H9Li) was added an ether solution of bis(pentafluorophenyl)chlorophosphine (0.1 mol).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Some New Phosphino Acetylenes

Carty¹,

Hota²,

Ng³

et al. 1971

Can. J. Chem.

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“…[12,13] The results obtained when "sasaposing" pentafluoro benzaldehyde 7 and the corresponding phenyl imine 8 [12] are summarized in Scheme 4.…”

Section: Resultsmentioning

confidence: 99%

Massive Electrostatic Effects on Heteropolar C–C Disconnections: Transforming a Phenyl Anion into a Potent Leaving Group

2005

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The SASAPOS protocol – a general reaction sequence which allows the complete exchange of various neutral ligands X in organic, elementorganic, and inorganic systems by cationic ligands L+ – has been applied to a small variety of pentafluoro benzene derivatives C6F5–E (E = –C(O)H, –C(N–Ph)H, –PCl2/–P(L+)2, –H) yielding the ion clusters C6(L+)5–E (F3CSO3–)5. The reaction conditions required to observe a heteropolar C–C or C–P disconnection, with a highly stabilized pentakisonio‐substituted phenyl anion as the key intermediate, are specified. When E = H, the latter compound also figures as the key intermediate during H/D exchange under basic conditions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

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Synthesis and Characterization of Some Perfluorophenylphosphine Derivatives

Cited by 45 publications

References 1 publication

The Bis(pentafluoroethyl)phosphinous Acid (C₂F₅)₂POH

The Bis(pentafluoroethyl)phosphinous Acid (C₂F₅)₂POH

Synthesis of Some New Phosphino Acetylenes

Massive Electrostatic Effects on Heteropolar C–C Disconnections: Transforming a Phenyl Anion into a Potent Leaving Group

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Synthesis and Characterization of Some Perfluorophenylphosphine Derivatives

Cited by 45 publications

References 1 publication

The Bis(pentafluoroethyl)phosphinous Acid (C2F5)2POH

The Bis(pentafluoroethyl)phosphinous Acid (C2F5)2POH

Synthesis of Some New Phosphino Acetylenes

Massive Electrostatic Effects on Heteropolar C–C Disconnections: Transforming a Phenyl Anion into a Potent Leaving Group

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The Bis(pentafluoroethyl)phosphinous Acid (C₂F₅)₂POH

The Bis(pentafluoroethyl)phosphinous Acid (C₂F₅)₂POH