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  • 1
    Electronic Resource
    Electronic Resource
    Cycloadditionsreaktionen von Organometallkomplexen, I. Die Synthese viergliedriger Metalla-Heterocyclen durch [2 + 2]-Cycloaddition aus (Isonitril)cobalt-Komplexen und Isocyanaten sowie Isothiocyanaten (1982)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 115 (1982), S. 3069-3084 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Cycloaddition Reactions of Organometal Complexes, I. The Synthesis of Four-membered Metalla-Heterocycles by [2 + 2] Cycloaddition of (Isonitrile)-cobalt Complexes and Isocyanates or IsothiocyanatesThe reaction of C5H5(PMe3)CoCNR (R = Me, Ph) with isocyanates OCNR' (R' = Me, Ph) leads to the metalla-heterocycles in nearly quantitative yields. The analogous four-membered ring compounds (4-6) are obtained from C5H5(PMe3)CoCNR (R = Me, Ph, c-C6H11) and SCNMe. In the reactions of C5H5(PMe3)CoCNtBu with SCNMe and of C5H5(PMe3)CoCNMe with SCNtBu the complex (4) is also formed. The X-ray structure analyses of 4 and 5 show the presence of planar four-membered CoCNC rings together with a trigonal-planar coordination of the corresponding C, N and C ring atoms. The protonation and methylation reactions of the metalla-heterocycles 1-5 yield diaminocarbene complexes, in most cases by preserving the four-membered CoCNC-ring. The structure of these complexes is discussed on the basis of their IR and NMR data.
    Notes: Die Reaktion von C5H5(PMe3)CoCNR (R = Me, Ph) mit Isocyanaten OCNR' (R' = Me, Ph) führt nahezu quantitativ zu den Metalla-Heterocyclen (1-3). Die analogen Vierring-Verbindungen (4-6) sind ausgehend von C5H5(PMe3)CoCNR (R = Me, Ph, c-C6H11) und SCNMe zugänglich. Bei den Umsetzungen von C5H5(PMe3)CoCNtBu mit SCNMe und von C5H5(PMe3)CoCNMe mit SCNtBu bildet sich ebenfalls der Komplex (4). Die Röntgenstrukturanalysen von 4 und 5 beweisen das Vorliegen planarer CoCNC-Vierringe mit ebenfalls trigonal-planar koordinierten C-, N- und C-Atomen. Die Protonierungs- und Methylierungsreaktionen der Metalla-Heterocyclen 1-5 ergeben -- in den meisten Fällen unter Erhalt der CoCNC-Vierringstruktur - Diaminocarben-Komplexe. Ihre Struktur wird anhand der IR- und NMR-Daten diskutiert.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19821150913
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  • 2
    Electronic Resource
    Electronic Resource
    Cycloadditionsreaktionen von Organometallkomplexen, IV. Nitrile als Synthesebausteine für Metalla-Heterocyclen: Neuartige cyclische Vinylcobalt- und (Aminocarben)cobalt(III)-Komplexe (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 1531-1544 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Cycloaddition Reactions of Organometal Complexes, IV. Nitriles as Building Blocks for Metalla-Heterocycles: New Cyclic Vinylcobalt and (Aminocarbene)cobalt(III) ComplexesThe reaction of [C5H5CoCH3(CNCH3)PMe3]I (2) or (3) with nitriles RCN (R = CH3, C6H5, CH = CH2, CH = CHMe, CMe = CH2, c-C3H5, NH2, NMe2, SMe) leads to the metalla-heterocycles (4-12) in nearly quantitative yields. The X-ray structure analysis of 4a (R = CH3, X = I) shows the presence of a planar five-membered CoCNCN heterocycle with the carbon atoms of the substituents at C, N, and C also in the ring plane. According to the bond lengths, the NCN unit of the ring can be well compared with the N = C — N skeleton of an amidine. Protonation of the compounds 4-12 yields the [amino(methyl)carbene]cobalt(III) complexes (17-25) which react with NaOMe to give again 4-12. The acidic nature of the CoC(CH3) and NH protons is also shown by deuteration experiments. Starting with C5H5Co(CNCH3) PMe3/CH3CN/C2H5I and C5H5Co(CNC6H5)PMe3/CH3 CN/CH3I, metalla-heterocycles containing the ring units CoC( = CHCH3)N, CoC(C2H5)N, C( = CH2)N(C6H5)C, and C(CH3)N(C6H5)C have also been prepared.
    Notes: Bei der Reaktion von [C5H5CoCH3(CNCH3)PMe3]I (2) oder (3) mit Nitrilen RCN (R = CH3, C6H5, CH = CH2 CH = CHMe, CMe = CH2, c-C3H5, NH2, NMe2, SMe) entstehen nahezu quantitative die Metalla-Heterocyclen 4-12). Die Röntgenstrukturanalyse von 4a (R = CH3; X = I) beweist, daß der fünfgliedrige CoCNCN-Heterocyclus völlig planar ist und auch die Kohlenstoffatome der Substituenten an C, N und C in der Ringebene liegen. Das Ring-NCN-Fragment ist aufgrund der Bindungslängen mit der N = C — N-Gruppierung eines Amidins gut vergleichbar. Die Protonierung der Verbindungen 4-12 führt zu den [Amino(methyl)carben]cobalt(III)-Komplexen (17-25), die mit NaOMe wieder zu 4-12 reagieren. Der acide Charakter der CoC(CH3)- und NH-Protonen wird auch durch Deuterierungsexperimente belegt. Ausgehend von C5H5Co(CNCH3)PMe3/CH3CN/C 2C2H5I und C5H5Co(CNC6H5)PMe3/CH3 CN/CH3I wurden ebenfalls Metalla-Heterocyclen mit den Ringbausteinen CoC( = CHCH3)N, CoC(C2H5)N, C( = CH2)N(C6H5)C und C(CH3)N(C6H5)C synthetisiert.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180420
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  • 3
    Electronic Resource
    Electronic Resource
    Cycloadditionsreaktionen von Organometallkomplexen, VI. Ein Dimetalla-Spiroheterocyclus durch zweifache [3 + 2]-Cycloaddition einer Imidoylcobalt-Einheit und CS2 (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 3151-3158 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Cycloaddition Reactions of Organometal Complexes, VI. Synthesis of a Dimetalla Spiroheterocycle by Twofold [3+2]-Cycloaddition of an Imidoylcobalt Unit and CS2The reaction of (1) with CS2 leads to the dimetalla spiroheterocycle 4, the structure of which has been determined by an X-ray structure analysis. 4 possesses crystallographic C2 symmetry. According to the structural parameters the bonding pattern in the five-membered CoCNCS rings corresponds more closely to that of a cyclic imidoyl than of a cyclic carbene complex. Compound (6), which is structurally similar to 1, has been prepared from 1 and thiobenzophenone by displacement of acetone.
    Notes: Bei der Reaktion von (1) mit CS2 entsteht der Dimetalla-Spiroheterocyclus 4, der durch eine Röntgenstrukturanalyse charakterisiert ist. 4 besitzt kristallographische C2-Symmetrie. Die Bindungsverhältnisse in den CoCNCS-Fünfringen entsprechen aufgrund der Strukturdaten eher denen eines cyclischen Imidoylals denen eines cyclischen Carben-Komplexes. Die mit 1 strukturell verwandte Verbindung wird aus 1 und Thiobenzophenon durch Verdrängung von Aceton hergestellt.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180814
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  • 4
    Electronic Resource
    Electronic Resource
    Cycloadditionsreaktionen von Organometallkomplexen, VII. Fünfgliedrige Cobalta-Heterocyclen durch [2 + 3]-Cycloaddition von Benzoylnitren an eine Co - CNR-Bindung (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 3932-3938 
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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: Cycloaddition Reactions of Organometal Complexes, VII. Five-membered Cobalta-Heterocycles by [2 + 3]-Cycloaddition of Benzoylnitrene to a Co — CNR BondThe reactions of the isonitrile compounds C5H5(PMe3CoCNR) 3b, R = Ph) with benzoyl azide leads to the metalla-heterocycles (4a, b). The X-ray structure analysis of 4b shows the presence of a nearly planar CoOCNC five-membered ring which presumably is formed by a [2 + 3]-cycloaddition of benzoylnitrene obtained from PhCON3 to the Co - CNR bond. The complexes 4a, b react with CF3CO2H/PF6- and [OMe3]BF4 by protonation and methylation, respectively, of the nitrogen atom of the metalla-heterocycles.
    Notes: Die Reaktionen der Isonitril-Verbindungen C5H5(PMe3CoCNR)3b, R = Ph) mit Benzoylazid führen zu den Metalla-Heterocyclen (4a, b). Die Röntgenstrukturanalyse von 4b beweist das Vorliegen eines nahezu planaren metallhaltigen Fünfrings, der vermutlich durch [2 + 3]-Cycloaddition des aus PhCON3 erhaltenen Benzoylnitrens an die Co - CNR-Bindung entstanden ist. Die Komplexe 4a, b reagieren mit CF3CO2H/PF6- und [OMe3]BF4 unter Protonierung bzw. Methylierung des Stickstoffatoms des Metalla-Heterocyclus.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851181006
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  • 5
    Electronic Resource
    Electronic Resource
    Cycloadditionsreaktionen von Organometallkomplexen, III. Fünfgliedrige Metalla-Heterocyclen durch [3 + 2]-Cycloaddition einer Imidoylcobalt-Einheit und einer Carbonylverbindung: Synthese, Struktur und Reaktivität (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 1517-1530 
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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: Cycloaddition Reactions of Organometal Complexes, III. Five-membered Metalla-Heterocycles by [3 + 2] Cycloaddition of a Imidoylcobalt Unit and a Carbonyl Compound: Syntheses, Structure, and ReactivityThe reaction of [C5H5CoCH3(CNCH3)PMe3]I with carbonyl compounds RR′C = O (R = R′ = CH3; R = H, R′ = CH3, C6H5) leads to the metalla-heterocycles (1-3) which are isolated as the iodide or PF6 salts. The X-ray structure analysis of the monohydrate of 1a (R = R′ = CH3; X = I) shows that the structural characteristics of the two parts (acetimidoyl ligand and acetone) forming the CoCNCO ring are partially preserved. The CoCNC part of the five-membered ring is nearly planar whereas the oxygen atom lies 34 pm out of this plane pointing towards the phosphane ligand. The protonation and methylation reactions of 1a and 2 (R = H, R′ = CH3; X = PF6) yield dicationic cyclic (aminocarbene)cobalt(III) complexes which in some cases react with excess of acid by ring cleavage and elimination of RR′C = O. In the reactions of 1b (X = PF6), [C5H5Co(η2-C(CH3)N-t-C4 H9)PMe3]I, and [C5H5Co(η1-C(CH3)NC6H 5)I] with PMe3 (and NH4PF6) the η1-imidoylcobalt(III) complexes [C5H5Co(η1-C(CH3)NR)(PMe3)2]PF6 (12-14) are formed, from which on protonation the (aminocarbene)cobalt(III) compounds [C5H5Co(C(CH3)NHR)(PMe3)2](PF 6)2 (15-17) are obtained.
    Notes: Die Reaktion von [C5H5CoCH3(CNCH3)PMe3]I mit den Carbonylverbindungen RR′C = O (R = R′ = CH3; R = H, R′ = CH3, C6H5) führt zu den Metalla-Heterocyclen (1-3), die in Form der Iodide oder PF6-Salze isoliert werden. Die Röntgenstrukturanalyse des Monohydrats von 1a (R = R′ = CH3; X = I) zeigt, daß die den CoCNCO-Fünfring bildenden Gruppen, Acetimidoyl-Ligand und Aceton, ihre strukturellen Charakteristika teilweise noch bewahrt haben. Die CoCNC-Einheit des Rings ist fast planar, während das Sauerstoffatom 34 pm außerhalb dieser Ebene auf der dem Phosphanliganden zugewandten seite liegt. Die Protonierungs- und Methylierungsreaktionen von 1a und 2 (R = H, R′ = CH3; X = PF6) ergeben dikationische cyclische (Aminocarben)cobalt(III)-Komplexe, die teilweise mit Überschuß an Säure unter Ringspaltung (und Eliminierung von RR′C = O) reagieren. Bei den Umsetzungen von 1b (X = PF6), [C5H5Co(η2-C(CH3)N-t-C4H 9)PMe3]I und [C5H5Co-(η1-C(CH3)NC6H5)PMe3)I] mit PMe3 (und NH4PF6) entstehen die η1-Imidoylcobalt(III)-Komplexe [C5H5Co(η1-C(CH3)NR)(PMe3) 2]PF6 (12-14), aus denen durch Protonierung die (Aminocarben)cobalt(III)-Verbindungen [C5H5Co(C(CH3)NHR)(PMe3)2] (PF6)2 (15-17) erhältlich sind.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180419
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  • 6
    Electronic Resource
    Electronic Resource
    Cycloadditionsreaktionen von Organometallkomplexen, V. Synthese tautomerer -Metalla-Heterocyclen aus Imidoylcobalt- Verbindungen und Isothiocyanaten (1985)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 118 (1985), S. 2282-2293 
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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: Cycloaddition Reactions of Organometal Complexes, V. Synthesis of Tautomeric Metallaheterocycles from Imidoylcobalt Compounds and IsothiocyanatesThe reaction of (3) or C5H5Co[C(CH3)=NPh]-(PMe3)I (5) with isothiocyanates SCNR (R = CH3, t-C4H9, C6H5, c-C6H11) leads to the novel five-membered metallaheterocycles 4, 6 - 12 for which two tautomeric forms (having an exocyclic = CH2 or an exocyclic = NR group) exist. The position of the equilibrium between the tautomers in solution depends on the substituent at the ring N-atom (CH3 or C6H5) as well as on the group R of the isothiocyanate. Protonation of the tautomers with CF3CO2H/NH4PF6 gives heterocyclic dicationic complexes of analogous constitution some of which are labile and in absence of excess acid react to regenerate the starting materials. Proton abstraction from the monocationic ring systems in 7, 8, 10, 12 with NaOMe produces the uncharged complexes (19 - 22) in which the three different building blocks C5H5-(PMe3)Co, S = C = NR, and H2C = C = NR′ are linked together to form a stable metallahetero-cycle.
    Notes: Bei der Reaktion von (3) oder C5H5Co[C(CH3)-=NPh](PMe3)I (5) mit Isothiocyanaten SCNR (R = CH3, t-C4H9, C6H5, c-C6H11) entstehen die neuartigen fünfgliedrigen Metalla-Heterocyclen 4, 6 - 12, die in zwei tautomeren Formen (mit exocyclischer =CH2- oder exocyclischer =NR-Gruppe) vorliegen. Die Lage des Tautomeren-gleichgewichts in Lösung hängt sowohl von dem Substituenten am Ring-N-Atom (CH3 oder C6H5) als auch von der Gruppe R des Isothiocyanats ab. Die Protonierung der Tautomeren mit CF3CO2H/NH4PF6 führt zu heterocyclischen dikationischen Komplexen gleichartiger Konstitution, die zum Teil in Abwesenheit freier Säure labil sind und wieder in die Ausgangsverbindungen übergehen. Durch Deprotonierung der monokationischen Fünfringe in 7, 8, 10, 12 mit NaOMe bilden sich die Neutralkomplexe (19 - 22), in denen die drei Bausteine C5H5(PMe3)Co, S = C = NR und H2C = C = NR′ zu einem stabilen Metalla-Heterocyclus verknüpft sind.
    Additional Material: 10 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19851180611
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  • 7
    Electronic Resource
    Electronic Resource
    Axially Dissymmetric Bis(triaryl)phosphines in the Biphenyl series: Synthesis of (6,6′-dimethylbiphenyl-2,2′-diyl)bis(diphenylphosphine) (‘BIPHEMP’) and analogues, and their use in Rh(I)-catalyzed asymmetric isomerizations of N,N-diethylnerylamine (1988)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 71 (1988), S. 897-929 
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    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The axially dissymmetric diphosphines (-)-(R)- and (+)-(S)-(6-6′-dimethylbiphenyl-2,2′-diyl)bis(diphenyl-phosphine) ((-)-(R)-10 and (+)-(S)-10; ‘BIPHEMP’) have been synthesized, starting from (R)- and (S)-6,6′-dimethylbiphenyl-2,2′-diamine ((R)- and(S)-16), respectively, via Sandmeyer reaction, liathiation, and phosphinylation. Moreover, racemic 4,4′- dimethyl- and 4,4′-bis(dimethylamino)-substituted analogues 11 and 12 respectively, and the 6,6′-bridged analogues 1,11-bis(diphenylphosphino)-5,7-dihydrodibenz[c,e]oxepin (13) were synthesized and resolved into optically pure (R)- and(S)-enantiomers via complexation with di-μ-chlorob is {(R)-2-[1-(dimethylamino)ethyl]pheny-C—N}dipalladium(II) ((R)-18). The molecular structures of the diphosphines (S)-10 and (R)-13 and of two derived cationic Rh(I) complexes,[Rh((S)- 10)(nbd)]BF4 and [Rh((R)- 13)(nbd)]BF4 were determined by x-ray analyses. Absolute configurations were established for (+)-(S)- 10 by X-ray analyses of both the free diphosphine and of the derived Rh(I) complex, and for (-)-(R)- 13 by X-ray analysis of the derived Rh(I) complex. Configurational assignments for the substituted BIPHEMP analogues 11 12 were achieved by means of 1H-NMR comparisons. The BIPHEMP ligand 10 and analogues 11, 12 and 13 are the first examples of optically active bis(triaylphosphines) containing the axially dissymmetric biphenyl moiety. All these new diphosphines proved to be excellent asymmetry-inducing ligands in Rh(I)-catalyzed isomerizations of N,N-diethylnerylamine affording citronellat enamine of 98-99% ee.
    Additional Material: 10 Ill.
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    URL: http://dx.doi.org/10.1002/hlca.19880710427
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  • 8
    Electronic Resource
    Electronic Resource
    Neuartige Bildungsweise von cis,trans-1,5-Cyclooctadien28. Mitteilung der Reihe „Kleine Ringe“. Diese Arbeit wurde von der Deutschen Forschungsgemeinschaft, dem Fonds der Chemischen Industrie und der BASF AG unterstützt.  -  27. Mitteilung: H.-D. Martin, R. Iden, H. J. Schiwek, Tetrahedron Lett., im Druck. (1978)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 90 (1978), S. 735-736 
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    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.19780900929
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  • 9
    Electronic Resource
    Electronic Resource
    Cobaltaheterocyclen durch [3 + 2]-Cycloaddition eines Acetimidoylcobalt-Komplexes mit Aceton und AcetonitrilBasische Metalle, 27. Mitteilung. Diese Arbeit wurde von der Deutschen Forschungsgemeinschaft, dem Fonds der Chemischen Industrie und durch Chemikalienspenden der BASF AG, Ludwigshafen, und DEGUSSA, Hanau, unterstützt. - 26. Mitteilung: [1].Professor Alfred Roedig zum 70. Geburtstag gewidmet (1981)
    Weinheim : Wiley-Blackwell
    Zeitschrift für die chemische Industrie 93 (1981), S. 305-306 
    Details
    ISSN: 0044-8249
    Keywords: Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/ange.19810930337
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  • 10
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    Electronic Resource
    Novel Mode of Formation of cis,trans-1,5-CyclooctadienePart 28 of the series “Small Rings”. This work was supported by the Deutsche Forschungsgemeinschaft, the Fonds der Chemischen Industrie, and BASF AG. - Part 27: H.-D. Martin, R. Iden, H. J. Schiwek, Tetrahedron Lett. 1978, 3337. (1978)
    Weinheim : Wiley-Blackwell
    Angewandte Chemie International Edition in English 17 (1978), S. 696-697 
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    ISSN: 0570-0833
    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/anie.197806961
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