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  • Wiley-Blackwell  (69)
  • 1
    Electronic Resource
    Electronic Resource
    Diastereoselective Substitution of PR3 for CO in Carbene(dicarbonyl)cyclopentadienyl Complexes of Manganese - Synthesis of (SMn)- and (RMn)-[Cp(CO)(PR3)Mn=C(OR*)R′] Complexes (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 339-347 
    Details
    ISSN: 1434-1948
    Keywords: Carbene complexes ; Carbyne complexes ; Asymmetric synthesis ; Carbohydrates ; Chiral auxiliaries ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chiral carbene complexes [Cp(CO)2Mn=C(OR*)Ph] (4a-e) were prepared by reaction of [Cp(CO)2Mn=C(OAc)Ph] (2) with HOR* [HOR* = 1,2:3,4-di-O-isopropylidene-D-galactopyranose (3a), 2,3,4,6-tetra-O-acetyl-D-galactopyranose (3b), 2,3,4,6-tetra-O-acetyl-D-glucopyranose (3c), (S)- (3d) and (R)-1,2-O-isopropylideneglycerol (3e)]. The replacement of a CO ligand with PTol3 in 4a-e proceeded diastereoselectively to give [Cp(CO)(PTol3)Mn=C(OR*)Ph] (5a-e). The diastereoselectivity increased in the order a, b, c, d: de = 8% (5a), 33% (5b), 70% (5c), 〉 96% (5d). For (R)-5d the isomer with the (S) configuration at manganese (SMn) was formed predominantly. For (S)-5d, only (RMn,S)-5d was detected (de 〉 96%). Photolysis of (R)-4d in the presence of phosphites or phosphanes afforded (SMn)-[Cp(CO)(PR3)Mn=C(OR*)Ph] [PR3 = P(OPh)3 (8), P(OMe)3 (9), P(OMe)2Ph (10), P(OMe)Ph2 (11), PPh3 (12), P(C6H4Cl-p)3 (13)] with a de 〉 96%. Photolysis of (S)-4d in the presence of P(OMe)3 gave (RMn,S)-9. Complex (R)-14 [related to (R)-4d] was obtained from [Cp(CO)2Mn=C(OAc)Tol-p] and 3d. Replacement of CO by PR3 in (R)-14 gave (SMn,R)-[Cp(CO)(PR3)Mn=C(OR*)Tol-p] [R = Tol-p (15), OMe (16), C6H4Cl-p (17)] with a de 〉 96%. In solution, the PTol3-substituted complex 5d is configurationally stable whereas the P(OMe)3 complex 9 epimerizes slowly at room temperature in CH2Cl2, Et2O, and THF within about one week.
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  • 2
    Electronic Resource
    Electronic Resource
    Polynuclear Complexes with Propynylidene C3-Bridges: General Synthetic Route to Bis-, Tris-, and Tetrakis(ethynylcarbene) Complexes (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 191-202 
    Details
    ISSN: 1434-1948
    Keywords: Polynuclear complexes ; Carbene complexes ; Bridging ligands ; Alkynyl complexes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The sequential reaction of two equivalents of the dimethylamino(ethynyl)carbene complexes [(CO)5M=C(NMe2)C≡CH] [M = W (1a), Cr (1b)] with two equivalents of nBuLi and one equivalent of a transition metal dichloride, [Cl2M′(Ln)], affords trinuclear biscarbene complexes of the type [(CO)5M=C(NMe2)C≡C-M′(Ln)-C≡CC(NMe)2=M(CO)5] [M′(Ln) = Ni(PEt3)2 (2a, b), Pd(PEt3)2 (3a, b), Pt(PEt3)2 (4a, b), Fe(dmpe)2 (6a), Hg (8a), Ti(η5-C5H5)2 (9a, b)] [dmpe = 1,2-bis(dimethylphosphino)ethane]. Treatment of 1a with equimolar amounts of first nBuLi and then [Cl2M′(Ln)] results in the formation of the monosubstitution products [(CO)5W=C(NMe2)C≡CM′(Ln)] [M′(Ln) = trans-Pd(PEt3)2Cl (5a), trans-Fe(dmpe)2Cl (7a)]. Additionally, the synthesis of the heterobimetallicethynylcarbene complex [(CO)5W=C(NMe2)C≡CPd(PEt3)2C≡CH] (10a), starting from 1a and [ClPd(PEt3)2C≡CH], is described. When three equivalents of 1a are treated, first with three equivalents of nBuLi and then with one equivalent of the trihalides PCl3 or BBr3, the novel tris(ethynylcarbene) complexes [{(CO)5W=C(NMe2)C≡C}3E] [E = B (11a), P (12a)] are obtained. The reaction of four equivalents of 1a,b with four equivalents of nBuLi, followed by addition of one equivalent of a group 14 tetrachloride [M′Cl4], yields the novel tetrakis(ethynylcarbene) complexes [{(CO)5M=C(NMe2)C≡C}4M′] [M′ = Si (13a, b), Ge (14a), Sn (15a, b)]. The complexes 8a, 9a, 12a, and 15a were characterized by X-ray structural analyses. All spectroscopic and structural data suggest that the carbene fragments and the central transition metal or heteroatom in these new bis-, tris-, and tetrakis(ethynylcarbene) complexes interact only weakly.
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  • 3
    Electronic Resource
    Electronic Resource
    Di-, Tri-, and Tetranuclear Cyclobutenylidene Complexes (1998)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1998 (1998), S. 1225-1234 
    Details
    ISSN: 1434-1948
    Keywords: Vinylidene complexes ; Cyclobutenylidene complexes ; Bridging ligands ; Cycloadditions ; Cross-coupling ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pentacarbonyl(dimethylvinylidene)chromium, [(CO)5Cr=C=CMe2] (1), reacts with the butadiynyl complexes [Cp(CO)2FeC≡CC≡CR] [2; R = SiMe3 (a), nBu (b), Ph (c)] and [Cp(CO)(PPh3)FeC≡CC≡CSiMe3] (3a) by regiospecific cycloaddition of the Cα≡Cβ bond of the butadiynyl complexes to the C=C bond of 1 to form the 1,3-heterobinuclear cyclobutenylidene complexes 4a-c and 5a with an alkynyl substituent at C-2 of the bridging ring. Desilylation of the 2-C≡CSiMe3 substituent in 4a and 5a with tetrabutylammonium fluoride affords the 2-C≡CH-substituted complexes 6 and 7. Complex 4a reacts with HNMe2 and HN(CH2)5 by substitution of NR2 for the 3-Fe(CO)2Cp fragment to form the corresponding 3-aminocyclobutenylidene complexes 10 and 11. Sequential reactions of 4a with [nBu4N]F and nBu3SnNEt2 give the trinuclear 2-C≡CSnnBu3-substituted complex 12. Coupling of 12 with C6H4I2-p yields the 2-C≡CC6H4I-p-substituted complex 13. Coupling of 7 with C6H4I2-p yields a mixture of the mono-coupling product 14 and the tetranuclear C≡C-C6H4-C≡C-bridged bis(cyclobutenylidene) complex 15. Coupling of 7 with trans-[(Et3P)2MCl2] in the presence of CuI/[Pd(PPh3)4] gives the trinuclear 2-C≡C-M(PEt3)2X-substituted complexes 16 (M = Pd, × = I) and 17 (M = Pt, × = Cl). The spectroscopic data as well as the results of the X-ray-structural analysis of 5a indicate strong electronic communication between the metal centers. In the solid state, 5a exhibits a “butterfly” conformation.
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  • 4
    Electronic Resource
    Electronic Resource
    Kinetische und mechanistische Untersuchungen von Übergangsmetallkomplex-Reaktionen, IV. Reaktionen von Komplexliganden, XVIII. Kinetik und Mechanismus der Einschiebung von 1-(Diethylamino)-1-propin in die Metall-Carbenkohlenstoff-Bindung von Pentacarbonyl(arylmethoxycarben)chrom(O) und -wolfram(O) (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 193-202 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Kinetic and Mechanistic Investigations of Transition Metal Complex Reactions, IV. Reactions of Complex Ligands, XVIII. Kinetic and Mechanism of the Insertion of 1-(Diethylamino)-1-propyne into the Metal-Carbene Bond of Pentacarbonyl(arylmethoxycarbene)chromium(0) and -tungsten(0)Pentacarbonyl(arylmethoxycarbene) complexes (CO)5M[C(p-C6H4R)OCH3] (M = Cr, W; R = CF3, Br, H, CH3, OCH3) (1a - g) add 1-(diethylamino)-1-propyne (2) via insertion of the alkyne into the metal-carbene bond. The formation of pentacarbonyl[(diethylamino)(2-aryl-2-methoxy-1-methylethenyl)carbene]chromium(0) and -tungsten(0) (3a - g) in octane follows a second-order rate law: d[3]/dt = k[1][2]. The tungsten complexes react faster than the analogous chromium compounds. Replacement of R = H by electron withdrawing substituents (CF3, Br) results in an increase, by electron donating groups (CH3, OCH3) in a decrease of the reaction rate. The activation enthalpies ΔH≠ are low (25.1 - 39.4 kJ · mol-1), the activation entropies ΔS≠ strongly negative (-129 to -145 J · mol- K-1). The results are discussed on the basis of an associative stepwise mechanism with an attack of the ynamine at the carbene carbon in the first reaction step.
    Notes: Pentacarbonyl(arylmethoxycarben)-Komplexe (CO)5M[C(p-C6H4R)OCH3] (M = Cr, W; R = CF3, Br, H, CH3, OCH3) (1a - g) addieren 1-(Diethylamino)-1-propin (2) unter Einschiebung des Alkins in die Metall-Carbenkohlenstoff-Bindung. Die Bildung von Pentacarbonyl[(diethylamino)(2-aryl-2-methoxy-1-methylethenyl)carben]chrom(0) und -wolfram(0) (3a - g) in Octan erfolgt nach einem Geschwindigkeitsgesetz zweiter Ordnung: d[3]/dt = k[1][2]. Die Wolframkomplexe reagieren schneller als die entsprechenden Chromverbindungen. Ersatz von R = H durch elektronenziehende Substituenten (Br, CF3) führt zu einer Erhöhung, durch elektronenspendende Gruppen (CH3, OCH3) zu einer Verringerung der Reaktionsgeschwindigkeit. Die Aktivierungsenthalpien ΔH≠ sind niedrig (25.1 - 39.4 kJ · mol-1), die Aktivierungsentropien ΔS≠ stark negativ (-129 bis -145 Jmol-1 K-1). Die Ergebnisse werden auf der Grundlage eines mehrstufigen Mechanismus mit einem Angriff des Inamins am Carbenkohlenstoff im ersten Reaktionsschritt diskutiert.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130120
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  • 5
    Electronic Resource
    Electronic Resource
    Vibrational Spectra of Organometallic Compounds. Von E. Maslowsky, Jr. John Wiley and Sons, Ltd., New York-London 1977. 1. Aufl., XII, 528 S., zahlr. Abb. und Tab., geb. £ 18.75 (1978)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 90 (1978), S. 574-575 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19780900735
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  • 6
    Electronic Resource
    Electronic Resource
    Ungewöhnliche Selektivität bei der thermischen Umlagerungs-Eliminierungsreaktion eines Carbenkomplexes in Lösung und im FestkörperProfessor E. O. Fischer zum 60. Geburtstag gewidmet (1978)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 90 (1978), S. 914-915 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19780901127
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  • 7
    Electronic Resource
    Electronic Resource
    Nachweis von Isomeren und intramolekulare Isomerisierung bei Carben-Komplexen des Chroms (1972)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 84 (1972), S. 682-683 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19720841408
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  • 8
    Electronic Resource
    Electronic Resource
    Kinetische und mechanistische Untersuchungen von Übergangsmetall-Komplex-Reaktionen, XV. Übergangsmetall-Schwefelylid-Komplexe, XX. Reaktionskinetischer Nachweis von [(CO)5Cr=CH2] bei der Umsetzung von Pentacarbonyl[(dimethyloxosulfonio)methanid]-chrom(0) mit tertiären Phosphanen (1984)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 117 (1984), S. 3340-3347 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Kinetic and Mechanistic Investigations of Transition Metal Complex Reactions, XV1). Transition Metal Sulfur Ylide Complexes, XX2). Kinetic Evidence of [(CO)5Cr=CH2] in the Reaction of Pentacarbonyl[(dimethyloxosulfonio)-methanide]chromium(0) with Tertiary PhosphanesPentacarbonyl[(dimethyloxosulfonio)methanide]chromium(0), (CO)5Cr[CH2S(O)Me2] (1), reacts with tertiary phosphanes PR3 (2) (R = Ph, C6H4OMe-(p), C6H4Me-(p), C6H4Cl-(p)) to give pentacarbonyl(phosphonium ylide)chromium(0) complexes, (CO)5Cr[CH2PR3] (3), and dimethyl sulfoxide according to the first-order rate law. The reaction rate is independent on the type of the phosphane. The activation parameters for the reaction in 1,1,2-trichloroethane in the temperature range 39.6 to 68.0°C are ΔH≠ = 28.1 kcal · mol-1 and ΔS≠ = 12.7 cal · mol-1 · K-1. The reaction is initiated by irreversible dissociation of OSMe2 from 1. Addition of 2 to the carbene carbon of the resulting pentacarbonylmethylenechromium, [(CO)5Cr=CH2], yields 3 in a fast succeeding step. A mechanism involving rate determining dissociation of the Cr=CH2 bond can be excluded. These results represent the first evidence of a neutral, electrophilic carbonylmethylene complex.
    Notes: Pentacarbonyl[(dimethyloxosulfonio)methanid]chrom(0), (CO)5Cr[CH2S(O)Me2] (1), reagiert mit tertiären Phosphanen PR3 (2) (R = Ph, C6H4OMe-(p), C6H4Me-(p), C6H4Cl-(p)) nach dem Geschwindigkeitsgesetz erster Ordnung zu Pentacarbonyl(phosphorylid)chrom(0)-Komplexen, (CO)5Cr[CH2PR3] (3), und Dimethylsulfoxid. Die Reaktionsgeschwindigkeit ist von der Art des Phosphans unabhängig. Die Aktivierungsparameter für die Reaktion in 1,1,2-Trichlorethan im Temperaturbereich von 39.6-68.0°C sind ΔH≠ = 28.1 kcal · mol-1 und ΔS≠ = 12.7 cal · mol-1. K-1. Die Reaktion wird durch irreversible Dissoziation von OSMe2 vom Komplex 1 eingeleitet. An das Carbenkohlenstoffatom des resultierenden Pentacarbonylmethylenchroms, [(CO)5Cr=CH2], addiert sich dann 2 in einem raschen Folgeschritt unter Bildung von 3. Ein Mechanismus über einen geschwindigkeitsbestimmenden Cr-CH2-Bindungsbruch kann ausgeschlossen werden. Diese Ergebnisse sind der erste Nachweis eines neutralen elektrophilen Carbonylmethylen-Komplexes.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19841171203
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  • 9
    Electronic Resource
    Electronic Resource
    Kinetische und mechanistische Untersuchungen von Übergangsmetallkomplex-Reaktionen, XVIII. Insertion von Diorganylcyanamiden in die Metall-Carbenkohlenstoff-Bindung - präparative und kinetische Untersuchungen (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 3683-3699 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Kinetic and Mechanistic Investigations of Transition Metal Complex Reactions, XVIII. Insertion of Diorganylcyanamides into the Metal-Carbene Bond - Preparative and Kinetic InvestigationsArylcarbene(pentacarbonyl) complexes, (CO)5M[C(Ph)R1] (M = Cr, Mo, W; R1 = Ph, OMe), react with diorganylcyanamides, R2R3N—C ≡ N (R2, R3 = Me, Et, Pr, iPr, Ph), via insertion of the C≡N group into the metal-carbene bond to give {[(arylmethylene)amino]-(diorganylamino)carbene}pentacarbonyl complexes, (CO)5M[C(NR2R3)N=C(Ph)R1]. The reaction follows a second-order rate law, first order each in the concentrations of the complex and the cyanamide. The rate constant increases slightly with increasing ability of the amino substituents R2 and R3 to donate electron density. The activation enthalpies are small (ΔH≠ = 37.5 to 40.6 kJ · mol-1), the activation entropies are strongly negative (ΔS≠ = -123 to -133 J · mol-1 · K-1). The reaction is initiated by nucleophilic attack of the cyanamide via the nitrile nitrogen at the carbene carbon.
    Notes: Arylcarben(pentacarbonyl)-Komplexe, (CO)5M[C(Ph)R1] (M = Cr, Mo, W; R1 = Ph, OMe), reagieren mit Diorganylcyanamiden, R2R3N—C ≡ N (R2, R3 = Me, Et, Pr, iPr, Ph), unter Einschiebung der C≡ N-Funktion in die Metall-Carbenkohlenstoff-Bindung zu den {[(Arylmethylen)amino](diorganylamino)carben}pentacarbonyl-Komplexen (CO)5M-[C(NR2R3)N=C(Ph)R1]. Die Reaktion erfolgt nach einem Geschwindigkeitsgesetz zweiter Ordnung, jeweils von erster Ordnung bezüglich der Komplex- und der Cyanamid-Konzentration. Die Geschwindigkeitskonstante nimmt mit steigender Donatorstärke der Amino-substituenten R2 und R3 geringfügig zu. Die Aktivierungsenthalpien sind niedrig (ΔH≠ = 37.5 bis 40.6 kJ · mol-1), die Aktivierungsentropien stark negativ (ΔS≠ = -123 bis -133 J · mol-1 · K-1). Die Reaktion wird durch einen nucleophilen Angriff des Cyanamids über den Nitril-Stickstoff am Carbenkohlenstoffatom eingeleitet.
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    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180922
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  • 10
    Electronic Resource
    Electronic Resource
    Metallaheterocumulene, VII α-Bromisocyanid-Komplexe durch Addition von Bromid an kationische 2-Azoniaallenyliden-Komplexe (1987)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 120 (1987), S. 811-814 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: The cationic [3,3-bis(tert-butyl)-2-azoniaallenylidene]pentacarbonyl complexes [(CO)5M(CNC(tBu)2)]⊖ AlBr4⊕ (2) [M=Cr (a), W (b)] which are synthesized by the reaction of (CO)5M-[C(OEt)N=C(tBu)2] (1) with AlBr3, react with tetrahydrofuran via addition of Br⊖ to give the isocyanide complexes (CO)5M-C≡N-C(tBu)2Br (3). Under nitrogen at room temperature, 3b decomposes in solution within ca. two hours to give the binuclear diisocyanide complex [(CO)5W-C≡N]2C(tBu)2 (4b). When the same conditions are applied to solutions of 3b in the presence of oxygen or of galvinoxyl 3b is stable. The structure of 4b was confirmed by an X-ray analysis.
    Notes: Die kationischen [3,3-Bis(tert-butyl)-2-azoniaallenyliden]pentacarbonyl-Komplexe [(CO)5M(CNC(tBu)2)⊖ (2) [M=Cr (a), W (b)] - darstellbar durch Umsetzung von (CO)5M[C(OEt)- N=C(tBu)2] (1) mit AlBr3 - reagieren mit Tetrahydrofuran unter Addition von Br⊕ zu den Isocyanid-Komplexen (CO)5M - C≡N-C(tBu)2Br (3). Bei Raumtemperatur zersetzt sich 3b unter Stickstoff in Lösung innerhalb von ca. zwei Stunden zu dem zweikernigen Diisocyanid-Komplex [(CO)5W-C≡N]2C(tBu)2 (4b), in Gegenwart von Sauerstoff oder von Galvinoxyl ist 3b unter ansonsten gleichen Bedingungen stabil. Die Struktur von 4b wurde durch eine Röntgenstrukturanalyse gesichert.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19871200520
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