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  • 11
    Electronic Resource
    Electronic Resource
    Alkylierungsreaktionen an Thioamiden, VI. Isolierung von E- und Z-Thioimidsäureestern (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 171-182 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Alkylation Reactions of Thioamides, VI. Isolation of E- and Z-ThioimidatesIn a sequence of stereospecific reactions the pure geometric isomers of ortho-substituted methyl thiobenzimidates 3 were prepared from the appropriate thiobenzamides 1. E/Z ratios and barriers to isomerization were determined by means of 1H NMR measurements.
    Notes: In einer Sequenz stereospezifischer Reaktionen wurden die reinen geometrischen Isomeren ortho-substituierter Thiobenzimidsäure-methylester 3 aus den entsprechenden Thiobenzamiden 1 dargestellt. Die E/Z-Verhältnisse und Isomerisierungsbarrieren wurden durch 1H-NMR-Messungen bestimmt.
    Additional Material: 8 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130118
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  • 12
    Electronic Resource
    Electronic Resource
    Absolute Configuration of 1,2,3,4-Tetrahydro-4-hydroxyisoquinolines (1987)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1987 (1987), S. 81-83 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Preparation, optical resolution, and absolute configuration of some 1,2,3,4-tetrahydro-4-hydroxyisoquinolines, including the major human metabolite of debrisoquine (4-hydroxydebrisoquine, 2), are described.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198719870115
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  • 13
    Electronic Resource
    Electronic Resource
    Synthese von (Pentafluorphenyl)diazomethan und 1-(Pentafluorphenyl)diazoethan (1985)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1985 (1985), S. 1711-1714 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Synthesis of (Pentafluorophenyl)diazomethane and 1-(Pentafluorophenyl)diazoethaneThe synthesis of the two new fluorinated diazoalkanes 2a and b is described.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198519850818
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  • 14
    Electronic Resource
    Electronic Resource
    2,3-Didehydrospartein (1989)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1989 (1989), S. 197-201 
    Details
    ISSN: 0170-2041
    Keywords: Didehydrosparteine ; Lupanine ; Sparteine ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: 2,3-DidehydrosparteineReduction of lupanine [(+)-6 or (→)-6] by use of diisobutylaluminium hydride (DIBAH) directly affords (+)-2,3-didehydrosparteine [(+)-3] and crystalline (±)-3, respectively, in 70% yield. The conjugate acid of 3 (iminium salt 2) is relatively stable and readily adds cyanide to give 2β-sparteinecarbonitrile (8). On the contrary, enamine 3 undergoes thermal 2±3′ dimerisation to give a diastereomeric mixture of 7. The identity of the title compound 3 with the major metabolite of (-)-sparteine (1) has been proven by use of gas chromatography/mass spectrometry.
    Notes: Die Reduktion von Lupanin [(+)-6 oder (→)-6] mit Diisobutylaluminiumhydrid (DIBAH) liefert in 70% Ausbeute direkt (+)-2,3-Didehydrospartein [(+)-3] bzw. kristallines Racemat (±)-3. Die konjugate Säure von 3 (Iminium-Salz 2) ist relativ stabil und addiert leicht Cyanid zu 2β-Sparteincarbonitril (8). Dagegen reagiert das Enamin 3 unter thermischer 2→3′-Dimerisierung zu einem Diastereomerengemisch von 7. Die Identität der Titelverbindung 3 mit dem Hauptmetaboliten von (-)-Spartein (1) wird durch Gaschromatographie/Massenspektrometrie belegt.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198919890138
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  • 15
    Electronic Resource
    Electronic Resource
    (S)-(-)- und (R)-(+)-1-(Pentafluorphenyl)ethanol (1986)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1986 (1986), S. 2004-2007 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: (S)-(-)- and (R)-(+)-1-(Pentafluorophenyl)ethanolThe preparation of enantiomerically pure (ee ≧ 94%) (S)-(-)- and (R)-(+)-1-pentafluorophenyl)ethanol [(S)-3 and (R) and (R)-3, respectively] by enantioselective synthesis and optical resolution is described.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198619861120
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  • 16
    Electronic Resource
    Electronic Resource
    über die Struktur der Thioamide und ihrer Derivate, XVII S-Aminierung sekundärer Thioamide zu α-Iminomethansulfenamiden (1971)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 753 (1971), S. 169-186 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On the Structure of Thioamides and their Derivatives, XVII1). S-Amination of Secondary Thioamides to α-IminomethanesulfenamidesSeveral secondary thioamides 1 have been treated with chloroamine to give α-iminomethanesulfenamides 8. IR- and NMR spectra of 8 indicate the occurrence of (E)/(Z) isomerism. Steric and electronic effects of the substituents on ΔG≠ values (table 1) prove an inversion mechanism for 8.
    Notes: Die Umsetzung sekundärer Thioamide 1 mit Chloramin führt zu α-Iminomethansulfenamiden 8, deren IR- und NMR-Spektren das Auftreten von (E)/(Z)-Isomerie zeigen. Die sterischen und elektronischen Effekte der Substituenten auf die ΔG≠-Werte (Tab. 1) beweisen den Inversionsmechanismus für 8.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.19717530115
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  • 17
    Electronic Resource
    Electronic Resource
    Über die Struktur der Thioamide und ihrer Derivate, XXXV1) Untersuchungen zur Stabilität der E- und Z-Konfigurationen bei Thiobenzhydroximsäure-methylestern und N-(Methoxy)-dithiokohlensäureimidesternHerrn Prof. Dr. Eugen Müller, Tübingen, zum 70. Geburtstag gewidmet. (1975)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1975 (1975), S. 1455-1464 
    Details
    ISSN: 0075-4617
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: On the Structure of Thioamides and Their Derivatives, XXXV). Studies on the Stability of the E- and Z-Configuration of Methyl Thiobenzohydroximates and N-(Methoxy)dithioimidocarbonatesBy irradiation with UV light the methyl thiobenzohydroximates (Z-1 may be converted to the thermic stable E-isomers. The kinetics of the acid catalyzed E ⇄ Z conversion shows that the free energy of activation for inversion at nitrogen (ΔG≥) must be higher than 24.3 kcal/mol (101.6 kJ/mol). In like manner D-NMR measurements indicate high barriers to inversion of ΔG≥ 25.5 kcal/mol) (106.7 kJ/mol) for N-(methoxy)dithioimidocarbonates 2. The dipole moment of (Z-1a was found to be 2.12 D whereas a lower dipole moment of 1.27 D was measured for the thermodynamically less stable (E-1a.
    Notes: Die Thiobenzhydroximsáure-methylester (E-1 können durch Bestrahlung mit UV-Licht in die thermisch stabilen E-Isomeren umgewandelt werden. Die Kinetik der säurekatalysierten E → Z Umwandlung zeigt, daβ die freie Aktivierungsenthalpie der Strickstoffinversion (ΔG≥) höher sein muβ als 24.3 kcal/mol (101.6 kJ/mol). Gleicherweise zeigen D-NMR- Messungen, daβ die N-(Methoxy)dithiokohlensäureimidester 2 hohe Isomerisierungsbarrieren von ΔG≥25.5 kcal/mol) besitzen. Das Dipolmoment von (Z)-1a beträgt 2.12 D, während für das thermodynamisch instabilere (E -1a ein niedrigeres Diplomoment von 1.27 D gemessen wurde.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.197519750723
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  • 18
    Electronic Resource
    Electronic Resource
    13C NMR of methyl N-methylthiobenzimidatesAlkylation Reactions of Thioamides, Part V. For Part IV see Ref. 1.. A novel approach to the interpretation of the relative 13C-E/Z shifts in amides and related compounds (1978)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 11 (1978), S. 612-616 
    Details
    ISSN: 0030-4921
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 13C NMR shifts of the E/Z mixtures of twelve, mainly ortho substituted, methyl N-methylthio-benzimidates have been completely assigned. The angles of twist about the aryl-imino-carbon bond were determined by means of the C-1 aryl shifts. Depending on the bulk of the ortho substituents the values vary from 18° in methyl 2-fluoro-N-methylthiobenzibenzimidate (Z) to 73° in methyl 4-bromo-N,2,6-trimethylthio-benzimidate (E). An explanation for the 13C-E/Z-N-alkyl and -S-alkyl resonances is facilitated by a new model which is initially based on the influence of electric fields. As this model is derived from amides, thioamides etc. it is possible to interpret the 13C-E/Z shifts in all related classes of compounds. The role of steric compression does not seem to be as important as was previously assumed.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1270111207
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  • 19
    Electronic Resource
    Electronic Resource
    Unusual 13C/77se couplings in the 13C NMR spectra of selenoimidates (1985)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 23 (1985), S. 327-329 
    Details
    ISSN: 0749-1581
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 13C NMR. chemical shifts of several selenoimidates (3) are reported in comparison with imidates (1) and thioimidates (2). Distinct resonance signals of 3 show additional satellites arising from 77Se couplings. Extremely large three-bond couplings [3J(13C77Se) = 28-39 Hz] are observed in the Z configuration of the N-methylselenoimidate double bond, where the coupling nuclei (77Se—C=N—13C) are cis-orientated.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1260230510
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  • 20
    Electronic Resource
    Electronic Resource
    Novel Syntheses of 2,3,4,5-Tetranor- and 6-oxo-Prostaglandins (1992)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1992 (1992), S. 1217-1223 
    Details
    ISSN: 0170-2041
    Keywords: Prostaglandin derivatives ; Lactones ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two short synthetic routes to the major metabolites of prostaglandins in man are reported. First, the 2,3,4,5-tetranorprostaglandins 1 and 2 are readily accessible by one-carbon homologation of γ-lactone 8 which involves the use of an ylide reagent, prepared from (1,3-dithian-2-yl)triphenylphosphonium chloride (9), subsequent cyclization of thioketene S,S-acetal 10 to spirotricyclic 11, and desulfurization to yield the required δ-lactone 12. Second, 6-oxoprostaglandins 3 and 4 are conveniently synthesized via α-acylation of the enolates of γ-lactones such as 22 followed by deprotection, hydrolysis, and decarboxylation of the resultant 3-oxocarboxylic acids. Both approaches have been realized with the synthesis of deuterated, racemic analogues of the prostaglandin metabolites.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1992199201203
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