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  • 1
    Electronic Resource
    Electronic Resource
    Eine neue Methode zur Knüpfung von P—P-Bindungen  -  Darstellung cyclischer Diphosphanmonosulfide (1988)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 121 (1988), S. 391-395 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: A New Method for the Formation of P—P Bonds  -  Synthesis of Cyclic Diphosphane MonosulfidesAttempts to synthesize the silyl ester of dimethylthiophosphorous acid Me2P—S—SiMe3 by treating diemthylphosphane sulfide Me2P(S)H with Me2N—SiMe3 almost quantitatively lead to the diphosphane monosulfide Me2P—P(S)Me2 (3b) besides (Me3Si)2S. If disecondary phosphane sulfide MeH(S)P—[CH2]n—P(S)MeH are employed instead of Me2P(S)H the monosulfides of the 1,2-diphospholanes or 1,2-diphosphinanes 7a and 7b, respectively, are obtained. Oxidative addition of tetrachloro-o-benzoquinone to 7a or 7b affords oxyphosphoranes with λ4P—λ5P bonds.
    Notes: Beim Versuch, Dimethylphosphansulfid Me2P(S)H durch Umsetzung mit Me2N—SiMe3 in den Silylester der Dimethylthiophosphorigen Säure Me2P—S—SiMe3 zu überführen, wurde neben (Me3Si)2S ausschließlich das Diphosphanmonosulfid Me2P—P(S)Me2 (3b) erhalten. Die Übertragung dieses Reaktionsprinzips auf die disekundären Phosphansulfide MeH(S)P—[CH2]n—P(S)-MeH (n = 3,4; 6a, b) macht die Monosulfide der 1,2-Diphospholane bzw. 1,2-Diphosphinane 7a bzw. 7b zugänglich. Oxidative Addition von Tetrachlor-o-benzochinon an 7a bzw. 7b liefert Oxyphosphorane mit λ4P—λ5P-Strukturelementen.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19881210302
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  • 2
    Electronic Resource
    Electronic Resource
    Reaktionen koordinierter Liganden, XIV. Synthese eines vierzähnigen Phosphor-Makrocyclus im Palladium(II)-Templat (1986)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 119 (1986), S. 349-365 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Reactions of Coordinated Ligands, XIV. Synthesis of a Tetradentate Phosphorus Macrocycle in a Palladium(II) TemplateCyclisation of the disecondary phosphane HMeP—CH2—CH2-PMeH (1) with o-xylylene dichloride within a PdII template affords tetradentate macrocyclic complexes (5a-c) as mixture of three diastereoisomers Recrystallisation from methanol yields the pure syn-(RSRS) isomer (5a · CH3OH). X-ray crystal structure determination (orthorhombic, space group P212121) reveals a 16-membered tetradentate ring system. The four phophorus atoms and one chlorine form a square pyramidal arrangement at palladium in the monocation [Pd(7)Cl]+ (Pd—P = 2.302(1), 2.304(1), 2.311(1), 2.306(1), Pd—Cl = 3.107(1)Å). Both seven-membered chelate ring systems adopt a chair configuration. If the palladium complexes 5a-c are treated with KCN, the macrocyclic ligand may be released from the template center and transferred to another transition metal (10, 11).
    Notes: Die Cyclisierung des disekundären Phosphans HMeP—CH2—CH2—PMeH (1) mit o-Xylylendichlorid im PdII-Templat liefert den Komplex des vierzähnigen makrocyclischen Liganden 7 in hoher Ausbeute als Gemisch dreier Stereoisomerer (5a-c). Umkristallisation aus Methanol liefert das syn-(RSRS)-Isomere in reiner Form (5a · CH3OH). Nach der Röntgenstrukturanalyse (orthorhombisch, Raumgruppe P212121) liegt im ionogen aufgebauten Komplex [Pd(7)Cl]+Cl-. CH3OH ein 16-gliedriges Ringsystem vor, das mit seinen vier P-Atomen die Basis der quadratisch pyramidalen Ligandenanordnung im Monokation bildet (Pd—P = 2.302(1), 2.304(1), 2.311(1), 2.306(1), Pd—Cl = 3.107(1)Å). Die beiden siebengliedrigen Chelatringe besitzen Sesselkonformation. Durch Behandeln der Palladiumkomplexe 5a-c mit KCN läßt sich der makrocyclische Ligand vom Templatzentrum ablösen und auf andere Übergangsmetalle übertragen (10, 11).
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19861190130
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  • 3
    Electronic Resource
    Electronic Resource
    Lineare Oligophosphaalkane, XV. Vierzähnige Phosphane in tetraedrischen und oktaedrischen Komplexen: Zink(II)- und Eisen(II)-Komplexe der linearen Tetraphosphaalkane Me2P—[CH2]3—PMe—[CH2]n—PMe—[CH2]3—PMe2 (n = 2, 3) (1986)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 119 (1986), S. 2921-2931 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Linear Oligophosphaalkanes, XV. Tetradentate Phosphanes in Tetrahedral and Octahedral Complexes: Zinc(II) and Iron(II) Complexes of the Linear Tetraphosphaalkanes Me2P—[CH2]3—PMe—[CH2]n—PMe—[CH2]3—PMe2 (n = 2, 3)With FeCl2 the linear tetraphosphaalkanes Me2P—[CH2]3—PMe—[CH2]n—PMe—[CH2]3—PMe2 (n = 2 (3), n = 3 (4)) form diamagnetic neutral iron complexes Fe(L)Cl2 (L = 3, 4). The reaction of Fe(3)Cl2 with CO or KCN yields isomeric mixtures of the carbonyl halide or dicyano complexes [Fe(3)(CO)Cl]+Cl- or Fe(3)(CN)2. By analysis of the 31P{1H} NMR spectra the structures are assigned to the isomers of the complexes obtained in these reactions. In aqueous solution zinc(II) nitrate with 3 forms a complex of composition Zn(3)(NO3)2 · 2H2O. The 31P{1H} NMR spectrum indicates that all donor atoms of the phosphane ligand are coordinated to the zinc(II) ion.
    Notes: Die linearen Tetraphosphaalkane Me2P—[CH2]3—PMe—[CH2]n—PMe—[CH2]3—PMe2 (n = 2 (3), n = 3 (4)) bilden mit FeCl2 diamagnetische, nicht ionogene Eisenkomplexe der Zusammensetzung Fe(L)Cl2 (L = 3, 4). Die Reaktion von Fe(3)Cl2 mit CO und KCN führt zu den Carbonylhalogenid- bzw. Dicyanokomplexen [Fe(3)(CO)Cl]+Cl- bzw. Fe(3)(CN)2. Die Analyse der 31P{1H}-NMR-Spektren erlaubt es, den im Isomerengemisch anfallenden Komplexen die Struktur von Diastereomeren bzw. Positionsisomeren zuzuordnen. Mit Zink(II)-nitrat bildet 3 in wäßrigem Medium einen Komplex der Zusammensetzung Zn(3)(NO3)2 · 2H2O. Das 31P{1H}-NMR-Spektrum des Racemats zeigt die Koordination aller vier P-Atome des Phosphanliganden an das Koordinationszentrum (Zn2+) an.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19861191003
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  • 4
    Electronic Resource
    Electronic Resource
    Lineare Oligophosphaalkane, XVI Achtgliedrige Ringverbindungen von Kupfer(I) und Silber(I) mit PH-funktionellen P - C - P-Brücken (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 81-87 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: With CuCl the secondary-tertiary methylenebisphosphane (iPr)2P - CH2 - P(iPr)H (1) forms a metal complex Cu2Cl2(1)2. The X-ray structural analysis of 2 (space group P21/a) shows a puckered eight-membered ring system formed by two ligands 1 and two trigonal planar Cu1 ions [Cu - P(1) 2.227(1), Cu - P(2′) 2.247(1), Cu - Cl 2.248(1) Å]. Reaction of 1 with AgBF4 or [Cu(CH3CN)4]PF6 leads to the formation of ionic complexes[Ag2(1)2[BF4]2 (4) or [Cu2(1)2(CH3CN)2][PF6]2 (3), repectively. The 1:2 complexes of 1 formed with CuCl or AgCl (5, 6) are assigned a dimeric structure M4Cl4(1)2 on the basis of mass spectroscopic and cryoscopic studies. Metal-ligand exchange observed in the temperature dependent 31P{1H}-NMR spectra of 6 is faster for the (iPr) HP-donor sit compared to the exchange reaction at the tertiary group (iPr)2P.
    Notes: Das Methylenbisphosphan (iPr)2P - CH2 - P(iPr)H (1) bildet mit CuCl einen neutralen Komplex (2) der Zusammensetzung Cu2Cl2(1)2. Nach den Ergebnissen der Röntgenstrukturanalyse (Raumgruppe P21/a) liegt in 2 ein gewelltes achtgliedriges Ringsystem vor, das aus zwei Liganden 1 und zwei CuI-Ionen mit trigonal planarer Koordination aufgebaut ist [Cu-P(1) 2.227(1), Cu - P(2′) 2.247(1), Cu - Cl 2.248(1) Å]. Die Umsetzung von 1 mit AgBF4 bzw. [Cu(CH3CN)4]PF6 führt zu ionogenen Komplexen [Ag2(1)2[BF4]2 (4) bzw. [Cu2(1)2(CH3CN)2][PF6]2 (3). Den 1:2-Komplexen von 1 mit CuCl und AgCl (5, 6) kommt nach massenspektroskopischen Untersuchungen und der kryoskopischen Bestimmung der Molmassen die Zusammensetzung M4Cl4(1)2 zu. Metall-Ligand-Austauschprozesse verlaufen an den (iPr)2P- und (iPr)HP-Gruppierungen in Ag4Cl4(1)2 (6) mit unterschiedlicher Geschwindigkeit ab, wie die Temperaturabhängigkeit der 31P{1H}-NMR-Spektren zeigt.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871200115
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  • 5
    Electronic Resource
    Electronic Resource
    Lineare Oligophosphaalkane, XIX1) Partielle Alkylierung von Phenylphosphan mit Dihalogenmethanen CH2X2 (X = Cl, Br) - eine einfache Synthese von Methylenbis(phenylphosphan), HPhP—CH2—PPhH (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 1707-1712 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Linear Oligophosphaalkanes, XIX1). - Partial Alkylation of Phenylphosphane with Dihalomethanes CH2X2 (X = Cl, Br) - A facile Synthesis of Methylenebis(phenylphosphane), HPhP—CH2—PPhHThe reaction of PhPHNa with CH2X2 (X = Cl, Br) in tetrahydrofuran affords methylenebis(phenylphosphane), HPhP—CH2—PPhH (2), phenylphosphane, methylphenylphosphane, PhPHMe, and 1,2,3,4-tetraphenylcyclo-5-carba-1,2,3,4-tetraphosphane, CH2(PPh)4 (3). HPhP—CH2—PPhH (2) may be obtained in a facile one-step synthesis with yields up to 70% by reaction of PhPH2 with CH2Cl2 and KOH in dimethyl sulfoxide/H2O or dimethylformamide/H2O. The formation of PhPHMe and CH2(PPh)4 may be explained by a reaction scheme including P-phenylphosphaalkene PhP=CH2 and HPhP—CH2Cl as reactive intermediates. The reactions between PhPHM (M = Na, K) and CH2Cl2 or CH2Br2, respectively, have been studied by independent experiments.
    Notes: Die Umsetzung von PhPHNa mit CH2X2 (X = Cl, Br) in Tetrahydrofuran liefert neben Methylenbis(phenylphosphan), HPhP—CH2—PPhH (2), Phenylphosphan, Methylphenylphosphan, PhPHMe, und 1,2,3,4-Tetraphenylcyclo-5-carba-1,2,3,4-tetraphosphan, CH2(PPh)4 (3). Auf überraschend einfache Weise und in Ausbeuten bis zu 70% gelingt die Synthese von HPhP—CH2—PPhH (2) durch Umsetzung von PhPH2 mit CH2Cl2 und KOH in Dimethylsulfoxid/H2O bzw. Dimethylformamid/H2O. Das Auftreten von PhPHMe und CH2(PPh)4 deutet auf die intermediäre Bildung des reaktiven P-Phenylphosphaalkens PhP=CH2 aus dem Primärprodukt HPhP—CH2Cl him. Der Ablauf der Reaktion zwischen PhPHM (M = Na, K) und CH2Cl2 bzw. CH2Br2 wurde durch unabhängige Experimente aufgeklärt.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871201016
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  • 6
    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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  • 7
    Electronic Resource
    Electronic Resource
    Lineare Oligophosphaalkane, XIV. Synthese und Struktur funktionalisierter 1,2,3,5-Diazadiphospholane (1986)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 119 (1986), S. 2767-2776 
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    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Linear Oligophosphaalkanes, XIV. Synthesis and Structure of Functionalized 1,2,3,5-DiazadiphospholanesThe methylenebisphosphanes RC1P—CH2—PC1R (1, 6a, b) (R = Cl, iPr, tBu) react with hydrazine, N,N′-dimethylhydrazine, or phthalohydrazide to give five-membered mono- or bicyclic hydrazinophosphanes 2-4, 7a, b, and 8. The unsymmetrically substituted bicyclic hydrazinophosphane 5 is accessible by a two-stage synthesis. On reaction of 6b with hydrazine the trans-isomer (racemic form) of 7b is formed significantly faster than the cis-isomer. At 60°C it rearranges within several hours to yield the thermodynamically stable trans-form. The X-ray structural analysis of 7b (monoclinic, space group P21/n; a = 1226.1(2), b = 593.32(7), c = 1745.2(2) pm,β = 90.46(1)°) shows a folded five-membered ring with the substituents in all-trans position on P and N (P1-C1 185.0(2), P2-C1 184.6(2), P1-N1 172.9(2), P2-N2 170.9(2), N1-N2 145.4(3) pm).
    Notes: Durch Umsetzung der Methylenbisphosphane RC1P—CH2—PC1R (1, 6a, b) (R = Cl, iPr, tBu) mit Hydrazin, N,N′-Dimethylhydrazin bzw. Phthalsäurehydrazid lassen sich fünfgliedrige mono- und bicyclische Hydrazinophosphane 2-4, 7a, b und 8 darstellen. Das unsymmetrisch substituierte bicyclische Hydrazinophosphan 5 ist in einer Zweistufenreaktion zugänglich. Das trans-Isomere (Racemat) von 7b bildet sich bei der Umsetzung von 6b mit Hydrazin wesentlich rascher als die cis-Verbindung (Mesoform). Sie lagert sich bei 60°C innerhalb weniger Stunden in das thermodynamisch stabilere trans-Isomere um. Die Röntgenstrukturanalyse von 7b (monoklin, Raumgruppe P21/n; a = 1226.1(2), b = 593.32(7), c = 1745.2(2) pm, β = 90.46(1)°) zeigt das Vorliegen eines gewellten Fünfrings mit all-trans- Position der Substituenten an P und N (P1 -C1 185.0(2), P2-C1 184.6(2), P1 - N1 172.9(2), P2-N2 170.9(2), N1 -N2 145.4(3) pm).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19861190909
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  • 8
    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 
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    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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  • 9
    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 
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    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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  • 10
    Electronic Resource
    Electronic Resource
    [Cu8(iPrPCH2PiPr)2Cl4(py)5], ein neuartiger Cu1-Cluster mit fünffach koordiniertem Phosphor in μ3-PRR′-Brücken (R = iPr, R′ = CH2PiPr)Professor Ulrich Wannagat zum 65. Geburtstag gewidmetLineare Oligophosphaalkane, 22. Mitteilung. Diese Arbeit wurde von der Deutschen Forschungsgemeinschaft und dem Fonds der Chemischen Industrie gefördert. - 21. Mitteilung: [5]. (1988)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 100 (1988), S. 1008-1009 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19881000740
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