Synthesis of triphenylphosphine oxide by oxidation of triphenylphosphine by oxygen under the catalytic effect of iron compounds

Vančová, V.; Ondrejkovičová, Iveta

doi:10.1135/cccc19830254

Cited by 15 publications

(10 citation statements)

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“…[15] Because PPh 3 could be oxidized to triphenylphosphine oxide with air in the presence of FeCl 3 , [16] we therefore examined the activity of triphenylphosphine oxide [(O)PPh 3 ] in the model reaction. Surprisingly, in this case, the reaction proceeded also very well (Table 1, entry 19).…”

Section: Resultsmentioning

confidence: 99%

Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three‐Component Reactions of Dimedone and an Aldehyde

2012

Adv Synth Catal

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Abstract:The selectivity of a three-component electrophilic reaction of an aldehyde with dimedone and another carbon-based nucleophile could be improved by a reversible alkylation procedure, which involves formation, breaking and regeneration of C À C bonds. In the presence of ironA C H T U N G T R E N N U N G (III) chloride and triphenylphosphine, an analogous C À C bond breaking can be observed in the reaction of 2,3,4,9-tetrahydro-9-(2-hydroxy-4,4-dimethyl-6-oxo-1-cyclohexen-1-yl)-3,3-dimethyl-1H-xanthen-1-one, in which the fragment of dimedone was replaced by a carbon-based nucleophile. Inspired by this observation, some three-component reactions of salicyldehyde and dimedone were successfully developed by using ironA C H T U N G T R E N N U N G (III) chloride and triphenylphosphine (PPh 3 ) as catalyst. PPh 3 plays the role of hydrogen bond acceptor, which confers a good flexibility of the substrate by weakening the intramolecular hydrogen bond, allowing thus an easy interaction of the substrate with ironA C H T U N G T R E N N U N G (III) chloride catalyst.

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Section: Resultsmentioning

confidence: 99%

Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three‐Component Reactions of Dimedone and an Aldehyde

2012

Adv Synth Catal

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“…These iron complexes are formed not only by direct synthesis from OPPh 3 and FeX 3 [5,6], but also by autocatalytic oxidation of PPh 3 by O 2 in the presence of some iron salts and X -anions [1][2][3][4]. This fact makes it possible to synthesise the above-mentioned complexes by various methods, differing in starting reactants and media.…”

Section: Iron(iii) Complexes Of the Composition [Fex 2 (Opph 3 ) 4 ][Fexmentioning

confidence: 99%

“…], where X is Cl or Br and OPPh 3 is triphenylphosphine oxide, act as catalysts for the oxidation of PPh 3 to OPPh 3 by O 2 at slightly increased temperature [1][2][3][4]. These iron complexes are formed not only by direct synthesis from OPPh 3 and FeX 3 [5,6], but also by autocatalytic oxidation of PPh 3 by O 2 in the presence of some iron salts and X -anions [1][2][3][4].…”

Section: Iron(iii) Complexes Of the Composition [Fex 2 (Opph 3 ) 4 ][Fexmentioning

confidence: 99%

“…For the structural study five samples were chosen ( Table 1). The samples CI and BI were prepared by direct synthesis from FeCl 3 and OPPh 3 in ethanol solution ____________________ * Corresponding author: e-mail: jorik@cvt.stuba.sk [5] while autocatalytic oxidation of PPh 3 by O 2 in the presence of FeX 3 (X = Cl or Br) in acetonitrile solution was used for preparation of the samples CII and BII [1,2].…”

Section: Synthesis and Analytical Proceduresmentioning

confidence: 99%

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X‐ray powder diffraction structural characterization of iron(III) chloro‐ and bromo‐complexes of triphenylphosphine oxide

Jorı́k¹,

Ondrejkovičová

Dreele

et al. 2003

Cryst. Res. Technol.

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Iron (III) complexes of the composition [FeX 2 (OPPh 3 ) 4 ] [FeX 4 ], where X is Cl or Br were synthesised by several methods. It was found that each particular synthesis has yielded solids with slightly different powder patterns and also their comparison to those of calculated from single crystal data showed remarkable differences. A series of constrained Rietveld refinements has been performed on the title complexes to explain these differences. In a course of Rietveld refinement it was found that preferred orientation is not the only factor affecting the shape of the pattern and atoms parameters were included into refinement too. The results of Rietveld refinement allowed to conclude that the structures of compounds prepared by different methods are identical. In addition, it was shown that also in the case of rather complicated structure like the title complexes the powder diffraction method can lead to reasonable results.

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“…d) 1m NaOH, THF/MeOH, 608, 8 h; 99%.boronate 16 (43%). To prevent the inhibition of the catalytic cycle of the planned Suzuki cross-coupling reaction [12], 16 was protected as the corresponding phosphane oxide 13 according to the method reported by Ondrejovic and co-workers[22], with an important modification. The transformation was achieved cleanly within 15 min by bubbling O 2 through a solution of 16 in MeCN at reflux in the presence of catalytic amounts (1 ± 2 mol-%) of Fe(SCN)…”

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confidence: 99%

Towards Asymmetric Catalysis in the Major Groove of 1,1′-Binaphthalenes

Lustenberger¹,

Diederich²

2000

HCA

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Four new diphosphane ligands, (R)-4, (R)-5, (S)-6, and (R)-7 (Schemes 3, 4, 6, and 7), featuring metalcoordination sites located in the major groove of chiral 1,1'-binaphthalene clefts, were prepared in enantiomerically pure form. The performance of this new class of ligands was tested in enantioselective, Pdcatalyzed allylic alkylation reactions with acyclic and cyclic methyl carbonates 28 ± 30 as substrates under various reaction conditions (Schemes 8 and 9). Using sodium phenyl sulfinate as a nucleophile, the reactivity of the catalysts formed with the new ligands and suitable palladium precursors was found satisfactory (> 90%); however, the ee values were in all cases poor (< 4%). Slightly better results were obtained using anions of dimethyl malonate as nucleophiles, but, also in these cases, the ee values never exceeded 17% (Table). 31 P-NMRSpectroscopic investigations revealed the formation of multiple-catalyst species in solution (Fig. 2), and molecular modeling suggested a lack of embedding of the coordinated substrate in a chiral pocket (Fig. 3), which probably accounts for the observed low level of enantioselectvity.

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Synthesis of triphenylphosphine oxide by oxidation of triphenylphosphine by oxygen under the catalytic effect of iron compounds

Cited by 15 publications

References 0 publications

Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three‐Component Reactions of Dimedone and an Aldehyde

Reversible Alkylation of Dimedone with Aldehyde: A Neglected Way for Maximizing Selectivity of Three‐Component Reactions of Dimedone and an Aldehyde

X‐ray powder diffraction structural characterization of iron(III) chloro‐ and bromo‐complexes of triphenylphosphine oxide

Towards Asymmetric Catalysis in the Major Groove of 1,1′-Binaphthalenes

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