Intern
    Prof. Dr. Reinhold Tacke

    Silicon-Containing Odorants

      

    The inside cover picture shows how by replacing the Si −CH2−CH2−Si group of disila-okoumal by a Si−CH2−Si or Si−O−Si unit, the volatility could significantly be improved to take full advantage of the C/Si exchange. The best 2R,4R-configured lower homologue (turquoise) overlaid on okoumal (green) is shown in front of an okoumé tree (photo courtesy of Roman Kaiser, Givaudan). For details see the communication by R. Tacke et al. on p. 315 ff.

    R. Tacke, J.B. Nätscher, N. Laskowski, P. Kraft, Lower homologs of okoumal and disila-okoumal: syntheses and olfactory  characterization of novel ambergris odorants, ChemBioChem 11, 315-319 (2010). Lesen Sie mehr ...

    Synthesis and olfactory characterization of novel silicon-containing acyclic dienone musk odorants

     

    M. Geyer, J. Bauer, C. Burschka, P. Kraft, R. Tacke,  Eur. J. Inorg. Chem. 2769-2776 (2011). more ...

     

    5,6-disubstituted 1,2,3-trisilaindanes as silicon analogues of phantolide-type musk odorants: synthesis, structure, reactivity, and olfactory properties

     

    J.B.G. Gluyas, C. Burschka, P. Kraft, R. Tacke, Organometallics 29, 5897-5903 (2010).

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    Sila-Substitution of Odorants

    • Olfactory Properties?       C/Si Bioisosterism?       Biological Sila-Substitution Effects?
    • More than a “me too!” approach: Sila-substitution can efficiently alter, and, ideally, optimize the olfactory properties of an odorant.
    • Limitation: “Chemistry rules” dictate whether or not and where silicon can be introduced.

     

    Differences between Analogous Compounds of Carbon and Silicon

    Shape and Size
    Bonding Geometries
    Conformational Flexibility
    Charge Distribution
    Lipophilicity
    Chemical Reactivity, etc.

     

    Review: R. Tacke, S. Metz, Chemistry & Biodiversity 2008, 5, 920–941.

    L. Doszczak, P. Kraft, H.-P. Weber, R. Bertermann, A. Triller, H. Hatt, R. Tacke, Angew. Chem. 2007, 119, 3431–3436; Angew. Chem. Int. Ed. 2007, 46, 3367–3371. Lesen Sie mehr

    M.W. Büttner, S. Metz, P. Kraft, R. Tacke, Organometallics 2007, 26, 3925–3929. Lesen Sie mehr

    M. W. Büttner, C. Burschka, K. Junold, P. Kraft, R. Tacke, ChemBioChem 2007, 8, 1447–1454. Lesen Sie mehr

    M.W. Büttner, M. Penka, L. Doszczak, P. Kraft, R. Tacke, Organometallics 2007, 26, 1295–1298. Lesen Sie mehr