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  • Organic Chemistry  (97)
  • Wiley-Blackwell  (97)
  • American Meteorological Society
  • 1995-1999  (33)
  • 1985-1989  (64)
  • 1
    Electronic Resource
    Electronic Resource
    Azobenzene-Based Photoswitchable Catenanes (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 649-656 
    Details
    ISSN: 0947-3440
    Keywords: Catenanes ; Interlocked rings ; Mechanical bond ; Photoswitches ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Four catenanes (1-4) and the corresponding tetracationic monocycles 5-8 are synthesized. X-ray structural analyses allow a prediction of the mobility (circumrotation) of the „interlocked“ rings in the catenanes, which is proven by 1H-NMR spectroscopy. An unexpected order in the crystal packing of 6 is demonstrated. (E/Z) isomerization in one ring influences the second ring of 1-4 and inversely. An existing obstacle inside the cavity of the switchable macrocycle can block this isomerization completely.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199519950491
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  • 2
    Electronic Resource
    Electronic Resource
    Steric Effects on Reaction Rates. VI. Application of a New MM2 Force-Field for Carbenium Ions to Solvolysis Rates of Secondary p-Toluenesulfonates (1985)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 68 (1985), S. 119-125 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An empirical force-field for carbenium ions has been incorporated in Allinger's MM2 programme. Structural parameters of secondary carbenium ions calculated by this method are compared with those obtained with Schleyer's BIGSTRN calculations. The strain changes occurring upon solvolysis of secondary p-toluenesulfonates are evaluated by means of this force-field and correlated with the rate constants for solvolysis. The equation for correlation of acetolysis, relative to cyclohexyl p-toluenesulfonate, of 28 kc substrates is ΔGrel+ = 0.67 ΔEst - 0.20 (r = 0.958).
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19850680115
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  • 3
    Electronic Resource
    Electronic Resource
    Rh-Catalyzed Oxidation of Anthracenes with tert-Butyl Hydroperoxide. Kinetic Aspects (1985)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 68 (1985), S. 450-455 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The polar effects of substituents on reactivity in oxidation of 2-substituted anthracenes with tert-butyl hydroperoxide (TBHP)/Rh(PPh3)3Cl have been investigated and compared with those obtained with TBHP/VO(acac)2 and chromic acid. The anthracene reactivities obtained from competition experiments are correlated with Hammett's σp-constants. The P-values are -2.60 for chromic acid and 0.72 for TBHP/VO(acac)2. A poor correlation with p = -0.17 (r = 0.756) was obtained for TBHP/Rh (PPh3)3Cl. It is concluded that the Rh-catalyzed reaction does not consist in electrophilic oxygen transfer to the anthracene.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19850680218
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  • 4
    Electronic Resource
    Electronic Resource
    The Chiral Glycine Enolate Derivative from 1-Benzoyl-2-(tert-butyl)-3-methyl-1,3-imidazolidin-4-one is Alkylated in the 5-Position with Relative Topicity lk. Preliminary Communication (1985)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 68 (1985), S. 949-952 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An overall enantioselective substitution of the R-group of an α-hydroxy- or α-amino acid 1 [R—CH(XH)COOH] by another R-group is possible through heterocycles 2 obtained from 1 with pivaladehyde (1 → 7). The rac- and the (S)-(+)-heterocycles 8 (title compounds of type 5) are prepared from glycine and O-benzyl-(S)-serine, respectively. Their enolates (cf. 9, type 6) are alkylated with iodomethane, iodobutane, 2-iodopropane, benzyl bromide, and acetone to give the trans-disubstituted imidazolidinones 10 with ≥ 95% diastereoselectivity. The configuration of the products is established by chemical correlation with alanine, phenylalanine, and valine.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19850680418
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  • 5
    Electronic Resource
    Electronic Resource
    Thermal Rearrangement of 5,6-Epimino-5,6-dihydro-β-ionone and Derivatives (1985)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 68 (1985), S. 1107-1113 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Thermolysis of 5,6-epimino-5,6-dihydro-β-ionone (1) and its N-methyl derivative (2) leads to their monocyclic isomers 6 and 10, respectively, presumably due to a direct [1,5]-H shift; on prolonged heating, these isomers are converted easily into pyrrole derivatives. In contrast, the thermoisomer 12 resulting from 5,6-(N-methoxycarbonyl)epimino-5,6-dihydro-β-ionone (3) by the same mechanism, does not undergo further ring transformation, but equilibrates with its more stable tautomer 13.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19850680504
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  • 6
    Electronic Resource
    Electronic Resource
    Complexes of 2,2′,2″-Nitrilotriphenol. Part 1. A Study of Bimolecular Nucleophilic Substitution at the Boron Atom (1987)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 70 (1987), S. 499-510 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The tetradentate ligand 2,2′,2″-nitrilotriphenol forms a boron complex III with an intramolecular, transannular N→B dative bond of 1.68 Å in a strained tricyclo[3.3.3.0]undecane chelating system. The complex reacts with nitrogen bases L, such as pyridine, quinuclidine and others, to form complexes III-L, in which the intramolecular B-N bond is replaced by one between B and the external nucleophile. In solution, this displacement reaction is reversible. It was studied by temperature-dependent NMR spectroscopy. The resulting reaction and activation parameters suggest that the reaction is a bimolecular nucleophilic substitution (SN2).
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19870700303
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  • 7
    Electronic Resource
    Electronic Resource
    Complexes of 2,2′,2″-Nitrilotriphenol. Part 3. Crystal and Molecular Structures of Three Aluminium Complexes (1987)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 70 (1987), S. 520-533 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Crystal and molecular structures of three Al(III) complexes of the tripod ligand 2,2′,2″-nitrilotriphenolate (I) are presented. They all show 5-coordinate Al in approximately trigonal bipyramidal geometry, with an external nucleophile X occupying the second axial position. X is OH- in[Al(I)(OH)]-[Hquin]+ (quin = quinuclidine), N in [Al(I)(py)] (py = pyridine), and one of the O-atoms of a second molecule in the dimeric [(Al(I))2]. Correlated variations in the axial bond lengths of the trigonal bipyramid are observed: [(Al(I))2]: Al-Nint. = 2.094 Å, Al-Oext. = 1.850 Å; [Al(I)(py)]: Al-Nint. = 2.153 Å, Al-Next., = 1.992 Å; [Al(I)(OH)]-: Al-Nint. = 2.278 Å, Al-Oext. = 1.765 Å. They are interpreted in terms of a dissociative reaction path at the Al(III) centre.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19870700305
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  • 8
    Electronic Resource
    Electronic Resource
    Steric Effects on Reaction Rates. Part VIII. The Significance of Front Strain Release in Solvolysis of Bridgehead Derivatives (1986)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 69 (1986), S. 635-645 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The steric requirements of leaving groups for 14 bridgehead derivatives have been examined using MM2 calculations. The strain varies almost monotonously throughout the series upon variation of the leaving group from H to C1, OH, CH3, CH3CH2O, (CH3)3CO, (CH3)3C and no significant trends for differential F-strain effects are detected expect for the perhydrophenalene derivative 13. The experimental rates of solvolysis of bridgehead derivatives correlate well with the calculated steric energy differences between substrate R-X and the corresponding carbenium ion R⊕. However, the strain calculations using the more recent force-fields (MM2) disagree, in part, with those reported in the literature: chloride and p-toluenesulfonate leaving groups correlate with identical slopes, and the perhydrotriquinacene derivative 10 shows no anomalous behavior. The calculations suggest that F-strain and C,C-hyperconjugation should not play any dominant role in bridgehead solvolysis.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19860690314
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  • 9
    Electronic Resource
    Electronic Resource
    Photochemical Rearrangements of 5,6-Epimino-5,6-dihydro-β-ionone and Derivatives (1986)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 69 (1986), S. 692-697 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: On irradiation at -20°, 5,6-epimino-5,6-dihydro-β-ionone (E)-3 rearranges to the products 6 and 7. The N-methyl derivative (E)-4 does not lead to any photoproduct upon brief irradiation; on prolonged irradiation, only unspecific photodecomposition is observed. The N-acylated derivative (E)-5 undergoes rapid (E)/(Z)-isomerization and slow rearrangement to 12 and 13.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19860690320
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  • 10
    Electronic Resource
    Electronic Resource
    Approaches to 1H-Cyclopropa[l]phenanthrenes. Eliminations with 1a,9b-Dihydro-1H-cyclopropa[l]phenanthrene Derivatives (1986)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 69 (1986), S. 855-864 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Base-induced elimination of the sulfonium salt 2i in the presence of furan affords the addition products 7 and 8, derived from 1H-cyclopropa[l]phenanthrene (1) and the isomeric cyclopropene 5a (Scheme 3). Upon oxidation, the selenide 2c yields phenanthrene-9-methanol (9), presumably via 1. No evidence for the intermediate 1 is obtained from sulfoxide pyrolysis with 2e, which leads to products formed by radical pathways (Scheme 5). Reductive elimination of the disulfone 3b gives half-reduction to monosulfone 2g and complete reduction to cyclopropane 2 as well as 9-methylphenanthrene (15), but no evidence for the intermediate 1.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19860690412
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