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  • 1
    Electronic Resource
    Electronic Resource
    Mass spectrometric studies on azidomorphine derivatives (1974)
    Chichester : Wiley-Blackwell
    Biological Mass Spectrometry 9 (1974), S. 847-853 
    Details
    ISSN: 0030-493X
    Keywords: Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The mass spectrometric behaviour of nine azidomorphine derivatives have been studied. These compounds proved to have surprisingly specific and selective fragmentation under electron-impact. For 6-deoxy-6-azido-dihydro-isomorphine derivatives (I to V) the main decomposition pathway involves the loss of an N2 molecule followed by a very rapid and selective fragmentation process. On the other hand, the molecular ions of 6-deoxy-8-azido-pseudomorphine derivatives (VI to VIII) and 6-deoxy-6-azido-14-hydroxy-isocodein (IX) primarily decompose by loss of the N3 radical. This is due to the allylic effect of the double bond in ring C, corresponding to the chemical behaviour of these compounds.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/oms.1210090904
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  • 2
    Electronic Resource
    Electronic Resource
    Reactions of Nepenthone with Chromium(II) Reagents in Neutral Aqueous Medium (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 149-153 
    Details
    ISSN: 1434-193X
    Keywords: Morphine alkaloids ; 6,14-Ethenomorphinans ; Chromium(II) complex reagents ; Organochromium(III) complex intermediates ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -A synthetic method for the selective transformations of a selected morphine alkaloid in neutral aqueous medium is introduced. Full diastereoselectivity was achieved by the transformation of nepenthone (1) with [Cr(ida)(H2O)3] into 2a (20R) showing a complementary method as compared to the reactions with classical reagents to result in 2b (20S). A new unexpected morphine derivative 3 was prepared by a ligand-induced modification of the reaction which involves an unprecedented rearrangement.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Substituent-dependent conformational changes in 6β-substituted codeine derivatives (1992)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 30 (1992), S. 552-557 
    Details
    ISSN: 0749-1581
    Keywords: Morphine alkaloids ; Isocodeines ; Conformation of ring C ; 13C and 1H NMR ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Complete 1H and 13C NMR data are reported for eleven isocodeine and seven dihydroisocodeine derivatives bearing various substituents at position 6. In isocodeines having bulky succinimido or phthalimodo groups at C-6 ring C adopts a half-boat conformation, characterized by the quasi-equatorial orientation of the C-6—N bond. The distortion from the usual boat form is due to steric interactions between C-14 and β-substituents at C-6, and it is greater in 14-hydroxy derivatives than in isocodeines unsubstituted at this position. In dihydroisocodeines the conformation of ring C is close to a chair, irrespective of the steric demand of the substituent at C-6.
    Additional Material: 5 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1260300617
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