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  • 1
    Electronic Resource
    Electronic Resource
    Acid-catalysed rearrangement of tetracyclo[4.3.0.02,9.04,8]nonane skeleton to substituted brendene derivatives (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1885-1889 
    Details
    ISSN: 0947-3440
    Keywords: 2-exo-Substituted brendene derivatives ; 2,5-Disubstituted brendene derivatives ; Cyclopropylcarbinyl cation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of 2-exo-substituted brendene derivatives 3a, 5a and 6 as well as 2,5-disubstituted brendene derivative 7 is described, starting from the readily available tetracyclo-[4.3.0.02,9.04,8]nonanone 1. The cationic rearrangement reactions of tetracyclic skeleton of 1 and 2 have been studied. The mechanism of these reactions is discussed. The preparation of inaccessible exo-alcohol 2a by reduction of ketone 1 is presented.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199510264
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    Paper (German National Licenses)
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis and Properties of a Bis(2-buteno)-Bridged Bis(adamantane): X-ray and Molecular Dynamic Studies of the trans, trans Isomer (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 1231-1236 
    Details
    ISSN: 1434-193X
    Keywords: Bis(adamantane), bis(2-buteno)-bridged ; Synthesis ; Molecular dynamic studies ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the trans,trans isomer of the bis(2-buteno)-bridged bis(adamantane) 3 has been developed, and its structure was established by spectral and X-ray structure analysis. Since the results of dynamic NMR studies indicate that 3 is conformationally mobile and the transition-state free energy (ΔGc≠) required to interconvert two equivalent con-formers was estimated to be ca. 60 kJ mol-1, the lowest energy conformer was subjected to a molecular dynamic simulation at 323 K in the gas phase. Three conformations 3a, 3b and 3c were found. The conformations 3a and 3c have anti-oriented adamantane units, while in 3b the adamantane molecules occupy the syn conformation. By analysing the conformational processes in macrocyclic diene 3, it was found that the calculated conformation 3a with molecular symmetry of C2h is very close to that found in solution at -50 °C, but differs from that which was observed in the solid state by X-ray-crystallographic analysis.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
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