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  • 2-Methylene-d2-adamantane derivatives  (1)
  • Adamantane as a building block  (1)
  • Cyclopropylcarbinyl  (1)
  • Macrocyclic thioethers  (1)
  • 1
    Electronic Resource
    Electronic Resource
    Synthesis and X-Ray Structures of New Macrocyclic Thioethers (1994)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 127 (1994), S. 1327-1329 
    Details
    ISSN: 0009-2940
    Keywords: Macrocyclic thioethers ; Adamantane as a building block ; Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 4,6:12,14-Di(1,3-adamantano)-1,9-dithiacyclohexadecane (1), 4,6:12,14:20,22-tri(1,3-adamantano)-1,9,17-trithiacyclotetracosane (2), and 5,7:14,16-di(1,3-adamantano)-1,2,10,11-tetrathiacyclooctadecane (3) have been obtained by intermolecular cyclization of 1,3-bis(2-bromoethyl)adamantane (4) with thioacetamide using a high-dilution technique. The reaction is concentration-dependent. The crystal structures of 1, 2, and 3 have been determined by single-crystal X-ray diffraction.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19941270724
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis, Reactions, and Properties of 2,8-Didehydronoradamantane Derivatives (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1401-1406 
    Details
    ISSN: 1434-193X
    Keywords: 2,8-Didehydronoradamantane derivatives ; Cyclopropylcarbinyl ; Rearrangements ; Ring-opening reactions ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -2,8-Didehydronoradamantan-9-one (2) was readily prepared by oxa-di-π-methane photorearrangement of brend-4-en-2-one (1). Other new 9-substituted 2,8-didehydronoradamantanes have also been prepared from 2, [i.e. 2,8-didehydronoradamantan-9-ol (3) and tosylhydrazone 4] and the ring-opening reactions have been studied. In acidic media, 2,8-didehydronoradamantan-9-ol (3) rearranges to the corresponding 2-substituted brend-4-ene derivatives. Exclusive formation of exo-2-substituted brend-4-enes supports the formation of a bridged bicyclobutonium ion. However, treatment of ketone 2 with PCl5 proceeds through a concerted mechanism by cleavage of the C-1-C-2 bond in 2 to give exo-2,5-dichlorotricyclo[4.2.1.03,8]non-4-ene (6). The tricyclo[4.2.1.03,8]nonane skeleton was also obtained by photochemically induced electron transfer reduction of 2 and reduction of 2 with Li/NH3, as well as by reduction of tosylhydrazone 4 with both NaBH3CN and BH3 × THF. On the other hand, Wolff-Kishner reduction of 2 gave the non-rearranged product, 2,8-didehydronoradamantane (10).
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Deuterium isotope effects on nuclear shielding. Cross-ring effects in rigid cyclic molecules (1993)
    Chichester : Wiley-Blackwell
    Organic Magnetic Resonance 31 (1993), S. 903-905 
    Details
    ISSN: 0749-1581
    Keywords: 13C NMR ; 2-Methylene-d2-adamantane derivatives ; Deuterium isotope shifts ; Chemistry ; Analytical Chemistry and Spectroscopy
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Deuterium isotope effects on 13C NMR chemical shifts, (2H/1H)nΔ(13C), of 2-methylene-d2-adamantane, 4-methylene-d2-2-adamantanone and 6-methylene-d2-2-adamantanone are presented. Long-range effects (4Δ, 5Δ and 6Δ) in a range from 5 to - 23 ppb were observed. The results for 5Δ and 6Δ are explained in terms of cross-ring field effects resulting from the change of dipole due to deuterium substitution.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/mrc.1260311005
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