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  • 1
    Electronic Resource
    Electronic Resource
    Linear oligophosphaalkanes. 23. Novel copper(I) complexes with electron-deficient triply bridging secondary phosphido groups .mu.3-PRR' (R = isopropyl, tert-butyl, R' = CH2-P R2; R = R' = phenyl) (1990)
    s.l. : American Chemical Society
    Inorganic chemistry 29 (1990), S. 2370-2375 
    Details
    ISSN: 1520-510X
    Source: ACS Legacy Archives
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1021/ic00337a034
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  • 2
    Electronic Resource
    Electronic Resource
    Lineare Oligophosphaalkane, XXV. Synthese von Ph2P—CH2—PH2 und (ph2P—CH2)2PH durch Phosphinomethylierung von PH3 unter Phasentransferkatalyse (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 995-999 
    Details
    ISSN: 0009-2940
    Keywords: Phosphine ; Phosphinomethylation ; Phase-transfer catalysis ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Linear Oligophosphaalkanes, XXV1. - Synthesis of Ph2P—CH2—PH2 and (Ph2P—CH2)2PH by Phosphinomethylation of PH3 with Phase-Transfer CatalysisAlkylation of Ph2PH with CH2Cl2 under phase-transfer conditions in the system dichloromethane/toluene/water affords Ph2P-CH2Cl in high yields. Depending on the reaction conditions employed Ph2P-CH2Cl reacts with PH3 in the two phase system under phase-transfer catalysis (nBu4NCl) to yield the tertiary-primary methylenebis(phosphane) Ph2P-CH2-Ph2 (2) or the PH functional triphosphaalkane Ph2P-CH2-PH-CH2-PPh2 (3), respectively. Metallation of 2 and 3 with RLi (R = nBu, tBu) and subsequent reaction with Me3siCl yields the silyl derivatives 2e and 3b, respectively. The analysis of the 1H- 13C- and 31P-NMR spectra is reported.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230511
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  • 3
    Electronic Resource
    Electronic Resource
    Neue Synthesen und Reaktionen von Phosphetaniumsalzen mit planarem Gerüst (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 1987-1997 
    Details
    ISSN: 0009-2940
    Keywords: Phosphetanium salts ; Phosphoranes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Novel Syntheses and Reactions of Phosphetanium Salts with a Planar SkeletonCleavage of the P-Si bond of silylphosphanes R2P-SiMe3 (R = iPr, tBu, 2,4,6-Me3C6H2) with excess 1,3-dihalogenpropanes X-[CH2]3-X (X = Br, I) affords phosphetanium salts (3) in good yields. These strained four-membered ring systems are also obtained by alkylation of secondary phosphanes R2PH with X-[CH2]3-X followed by deprotonation of the intermediate phosphonium salts [R2P(H) - [CH2]3-X]+ X- (R e.g. tBu; X = Br, 7b). Silylphosphanes and secondary phosphanes with less bulky substituents preferably form open-chain phosphonium salts with [CH2]3-X or allyl substituents in these reactions. X-ray structural analysis of (3h) reveals planar geometries for the PC3 skeletons of the cations. The reactivity of 3b towards different types of nucleophiles [F-, NH2-, OH-, OR-, Fe(CO)2Cp-, NaN(SiMe3)2, RR′PLi] has been studied. Reaction with CsF or NaNH2, leads to a stable monofluoro or monoamino phosphorane, respectively, with cyclic four-membered PC3 skeletons. In all other cases opening of the phosphetanium ring system occurs leading to derivatives with R2P - [CH2]3 terminal groups. Bidentate and polydentate ligands, e.g. 19-25, with bulky substituents in terminal position have been synthesized in high yields by cleavage of 3b with mono- and bifunctional lithium phosphides. By deprotonation of 3b with MeLi the cyclic ylide 14 is formed. Treatment with acetone or benzaldehyde leads to the unsaturated open-chain phosphane oxides 15a or 15b in a Wittig-type reaction.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250904
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  • 4
    Electronic Resource
    Electronic Resource
    Enthalogenierung und regioselektive Phosphiniden-Fragmentierung unsymmetrisch substituierter Methylenbisphosphane RXP-CH2-PXR′ mit Fe2(CO)9 (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 1999-2006 
    Details
    ISSN: 0009-2940
    Keywords: Methylenebisphosphanes ; Clusters ; Phosphinidene fragmentation ; Regioselectivity ; Phosphaalkene ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Dehalogenation and Regioselective Phosphinidene Fragmentation of Unsymmetrically Substituted Methylenebisphosphanes RXP-CH2-PXR′ with Fe2(CO)9Reductive dehalogenation of the unsymmetrically substituted methylenebisphosphanes RXP-CH2-PR′X [X = Cl, Br; R = tBu, NEt2; R′ = 2,4,6-R”3C6H2 (R” = Me, tBu), NEt2, 2,6-iPr2C6-H3O, 2,6,4-tBu2MeC6H2O] with Fe2(CO)9 affords, depending on the reaction conditions employed, phosphido complexes [μ2-(RP-CH2-PR′)]Fe2(CO)6 (2) or phosphaalkene clusters (μ3-PR′)(η2,μ3-PRCH2)Fe3(CO)9(6) or [(μ-PR)(η2,μ3PR′CH2)]Fe3-(CO)9 (7), respectively, by regioselective phosphinidene fragmentation of the RP-CH2-PR′ skeletons. The unstable cluster compounds [μ3-PR′-CH2-PR)]Fe3(CO)9 (4) are formed as intermediate products. X-ray structural analysis of 6c (R = tBu; R′ = NEt2) reveals a flat butterfly (μ3-PR)Fe3 structure bridged by the phosphaalkene ligand tBuP = CH2 with a short P = C distance [177.2(4) pm].
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250905
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  • 5
    Electronic Resource
    Electronic Resource
    Lineare Oligophosphaalkane, XXIV Synthese und strukturelle Charakterisierung von Cu8-Mehrkernkomplexen mit Elektronenmangel-Phosphidobrücken (1990)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 123 (1990), S. 653-659 
    Details
    ISSN: 0009-2940
    Keywords: Copper complexes, Cu8/Phosphido bridges/Oligophosphaalkanes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Linear Oligophosphaalkanes, XXIV. - Syntheses and Structural Characterisation of Cu8 Complexes with Electron-Deficient Phosphido BridgesReaction of silylphosphanes (Me3Si)RP-CH2-PR(SiMe3) (R = iPr, tBu, 2,4,6,-Me3C6H2) with four equivalents of copper(1) halides CuX (X = Cl, Br) or a mixture of two equivalents of CuCl and Cul in the presence of pyridine as an auxiliary ligand affords octanuclear copper(1) complexes of composition Cu8X4(RP-CH2-PR)2(Py)n(CH3CN)m (n = 5, m = 0; n = 4, m = 1; X = Cl, Br, I). Multinuclear compounds of this type may also be obtained by deprotonation of the disecondary phosphanes HRP-CH2-PRH (R = iPr, Ph, 2,4,6-Me3C6H2) with strong organic bases (DBU) in the presence of CuCl and pyridine. The X-ray structural analysis of Cu8Cl4(iPr-P-CH2-PiPr)2(Py)5 (3a) (space group P21/c) reveals a Cu4(P-C-P)2 skeleton to which four CuCl(Py)n units (n = 1, 2) are coordinated by Cu-Cl and Cu-P bridges. The phosphorus atoms of the electron-deficient μ3-PRR′ bridges formed thereby show a distorted trigonal bipyramidal coordination with almost planar PCu3 units. Due to the multiple bridging of the Cu(I) ions in 3a the Cu⃛Cu distances in the Cu8 complex are relatively short (247.1-276.5 pm).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19901230402
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  • 6
    Electronic Resource
    Electronic Resource
    Reaktionen koordinierter Liganden, XVIII. Templatsynthesen und Peripheriereaktionen makrocyclischer Multiphosphanliganden mit funktionellen Gruppen (1992)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 125 (1992), S. 1785-1794 
    Details
    ISSN: 0009-2940
    Keywords: Template synthesis ; Phosphane complexes, macrocyclic, tetradentate ; Periphery reactions ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Reactions of Coordinated Ligands, XVIII. - Template Syntheses and Periphery Reactions of Macrocyclic Multiphosphane Ligands with Functional GroupsCyclisation of the tridentate phosphanes PhP([CH2]3PRH)2 (R = H, Me) with the divinyl components R′P(CH=CH2)2 [R′ = Ph, NEt2, O(iPr)] within Ni(II) templates affords complexes NiBr2L (3a-f) of functionalised macrocyclic tetraphosphanes (L) in almost quantitative yields. An X-ray structural analysis of the cyano complex [Ni(CN)L]PF6 (5a), obtained by metathetical reactions, reveals a folded 14-membered macrocyclic ligand L. The P atoms occupy axial and equatorial positions within the trigonal-bipyramidal ligand arrangement with an equatorial CN group. By periphery reactions at the P-NEt2 function of the 14-membered ring system P—OH, P—O-, P—Cl, P—OR″ derivatives (R″ = Me, iPr, CH2CH=CH2) are formed. Addition of methyl acrylate to the P—H functions in 3d and 3f leads to macrocyclic diesters 12a, 12b. By cleavage of the P—N bond in 3a with concentrated aqueous HBr a complex of composition 7a · HBr · 3 H2O is obtained. An X-ray structural analysis of the latter shows a P—OH functionalised macrocyclic tetraphosphane occupying the four basal positions within a square pyramidal coordination geometry at Ni(II).
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19921250802
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  • 7
    Electronic Resource
    Electronic Resource
    Synthese und Koordinationschemie hemilabiler P,N-Hybridliganden mit terminalen 2-Pyridyl-DonorgruppierungenHerrn Professor Dr. O. J. Scherer zum 60. Geburtstag gewidmet. (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 481-488 
    Details
    ISSN: 0009-2940
    Keywords: 2-Pyridylalkylphosphanes ; Hemilabile ligands ; Nickel complexes ; Palladium complexes ; Platinum complexes ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis and Coordination Chemistry of Hemilabile P,N-Hybride Ligands with Terminal 2-Pyridyl Donor Groups*P,N-hybride ligands 1-7 containing terminal 2-pyridyl donor groups have been obtained by base-catalyzed addition of diphenylvinylphosphane or 2-vinylpyridine to primary or secondary phosphanes [2-Py-(CH2)2-PR′H (R′ = H, Ph), HMeP-(CH2)3-PMeH] or by alkylation of organolithium phosphides, R2P-(CH2)3-PMeLi or 2-Py-(CH2)2-PR′Li (R = Ph, iPr; R′ = H, Ph), with 2-(2-chloroethyl)pyridine or di-tert-butylphosphetanium bromide. Upon reaction with NiBr2 3 H2O or K2MCl4 (M = Pd, Pt) the phosphanes (L) of type 2-Py-(CH2)2-P(R′)-(CH2)m-PR2 (1, 3, 6) form square planar Ni(II), Pd(II), and Pt(II) complexes of composition MX2(L) (10-14). With NiBr2 and K2MX4 the tripod type phosphane 2 forms square pyramidal complexes [MX(2)]X (M = Ni, Pd; X = Cl, Br; 15, 16). An X-ray structural analysis of [NiBr(2)]+Br- (15) reveals a distorted square pyramidal coordination geometry at Ni(II), the 2-Py donor being in apical position with a long Ni—N bond [2.270(15) Å]. The tetradentate ligand 7 forms Ni(II), Pd(II), and Pt(II) complexes MX2(7) which for M = Pd, Pt show dynamic behaviour by exchange of the terminal Py donor groups. With [RhCl(COD)]2 the tridentate ligands L (1 and 3) yield complexes of composition RhCl(L) (20, 21). The structure of 20 has been determinated by X-ray diffraction. The ligand 3, acting in a tridentate manner, is coordinated to Rh(I) in a distorted square-planar arrangement with a normal Rh—N distance [2.145(3) Å].
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270306
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  • 8
    Electronic Resource
    Electronic Resource
    Wasserlösliche Phosphane, IV. Tertiäre Alkylphosphane mit Ammoniumgruppen in den Seitenketten - Amphiphile mit basischen P-Atomen (1995)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 128 (1995), S. 275-279 
    Details
    ISSN: 0009-2940
    Keywords: Aminoalkylphosphanes ; N-Quaternisation ; P-Alkylation ; Cationic tertiary phosphanes ; Amphiphiles ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Water-Soluble Phosphanes, IV. - Tertiary Alkylphosphanes with Ammonium Groups in the Side Chains  -  Amphiphiles with Basic P-AtomsBy stepwise aminoalkylation of PH3 with Me2N—(CH2)2—Cl in the superbasic medium DMSO/KOH the secondary phosphane [Me2N—(CH2)2]2PH (2) is obtained in good yields. Metallation of 2 with n-BuLi and subsequent reaction with Me2N—(CH2)2]2Cl affords the basic tertiary phosphane [Me2N—(CH2)2]2]3P (3), which on protonation with Ph3P · HBr in CH2Cl2 gives {[HNMe2 - (CH2)2]3P}3+ 3 Br- (4a) with an extremely high solubility in water. By oxidation of 3 with H2O2 and N-quaternisation with Me3O+ BF-4 the cationic phosphane oxide {[Me3N—(CH2)2]3P=O}3+ 3 BF-4 (5a) is formed, which could, however, not be reduced with SiHCl3 or Si2Cl6/NEt3 to the corresponding tricationic phosphane. Tertiary cationic phosphanes of type [RMe2N—(CH2)2—P(Oct)2]+ X- (8a, 8b, R = Me, C8H17; X = Br, I) are accessible by free radical addition of 1-octene to 7b and 7d. Addition of formaldehyde to 7a gives the hydroxymethyl phosphane 10a. By methylation of [RMe2N—(CH2)2—PH2]+I- (7d and 7e, R = CnH2n+1, n = 8, 12) with Mel under controlled condition and subsequent deprotonation of the phosphonium salts 12b and 12c the cationic tertiary phosphanes 13a and 13b with long alkyl side chains may be obtained in good yields.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19951280311
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  • 9
    Electronic Resource
    Electronic Resource
    Novel Syntheses of Mono- and Bisphosphonated Aromatic Phosphanes by Consecutive Pd-Catalyzed P-C Coupling Reactions and Nucleophilic Phosphanylation - X-ray Structure of Ph2P-C6H4-m-PO3Na2 · 5.5 H2O · iPrOH (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 1029-1034 
    Details
    ISSN: 1434-1948
    Keywords: Pd-catalyzed P-C coupling ; Nucleophilic phosphanylation ; Mono- and bisphosphonated phosphanes ; Monoesters ; Water solubility ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The triphenylphosphane derivatives 2a and 5, bearing one and two phosphonic ester groups, are accessible in high yields by consecutive Pd-catalyzed P-C coupling reactions of p-bromoiodobenzene with Ph2PH and PhPH2, respectively, and then with diethyl phosphite. Ester hydrolysis yields the highly water-soluble sodium salts of mono- and bis-phosphonated triphenylphosphane, 3a and 6, respectively. On reaction of the p- and m-fluorophenylphosphonic diethyl esters 7a, 7b with Ph2PK and subsequent ester hydrolysis the isomeric disodium (diphenylphosphano)phenylphosphonates 3a, 3b were obtained. The X-ray structure of Ph2P(C6H4-m-PO3Na2) · 5.5 H2O · iPrOH (space group Cmc21) has been determined. In the solid state, it forms a layer structure with hydrophilic (PO32-, H2O, iPrOH) and hydrophobic (Ph2P) compartments, in which the PO32- anionic groups are not engaged in coordination of the sodium cations.
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  • 10
    Electronic Resource
    Electronic Resource
    Nucleophilic Phosphanylation of Fluoroaromatic Compounds with Carboxyl, Carboxymethyl, and Aminomethyl Functionalities - an Efficient Synthetic Route to Amphiphilic Arylphosphanes (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 73-82 
    Details
    ISSN: 1434-1948
    Keywords: Nucleophilic phosphanylation ; Phosphanylphthalic acid ; Phosphanylphenylacetic acid ; Benzylaminophosphanes ; Water solubility ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chiral- and multiply-carboxylated phosphanes and phosphanyl derivatives of benzoic and phthalic acids (1-9) are accessible in high yields by nucleophilic phosphanylation of potassium or lithium salts of commercially available fluorobenzoic and 3-fluorophthalic acids with Ph2PH, Ph2PK, PhPLi2 Ph(K)P-(CH2)3-P(K)Ph in superbasic media (DMSO/KOH) or in THF and DME. The hitherto unknown phosphanylphenylacetic acids (10-13) and phosphanylbenzylamines RR′P-C6H4-CH2- NH2 (14-19, R, R′ = H, Me, Ph) with unsubstituted amino groups were also synthesized by this method. The diphenylphosphanyl derivatives 14-16 (R, R′ = Ph) are accessible by an alternative method involving LiAlH4 reduction of the phosphanylbenzonitriles (20-22), which were obtained in high yields by nucleophilic phosphanylation of the corresponding fluoro- or chlorobenzonitriles. The novel bidentate phosphanylbenzonitrile 23 has also been obtained using this synthetic route. All compounds were completely characterized by elemental analysis, NMR spectroscopy, and mass spectrometry.
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