Silicon-based noncyclic woody-ambery odorants: Synthesis and olfactory characterization of 4,4,6,6-tetramethylheptan-2-one and its sila-analogues

Organometallics

Volumn 26, Issue 16, 2007, Pages 3925-3929

  Büttner, Matthias W ^a   Metz, Stefan ^a   Kraft, Philip ^b   Tacke, Reinhold ^a  

^a UNIVERSITY OF WÜRZBURG   (Germany)

^b GIVAUDAN SCHWEIZ AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

DERIVATIVES; ORGANOMETALLICS; SILICON COMPOUNDS; SYNTHESIS (CHEMICAL); VAPOR PRESSURE;

ODORANTS; OLFACTORY PROPERTIES; THRESHOLD VALUES;

KETONES;

EID: 34547736945     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om700260q     Document Type: Article

References (19)

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2. Hong, S.; Corey, E. J. J. Am. Chem. Soc. 2006, 128, 1346-1352.
3. Kraft, P.; Frech, D.; Müller, U.; Fráter, G. Synthesis 2006, 2215-2223.
4. Recent publications: (a) Büttner, M. W.; Penka, M.; Doszczak, L.; Kraft, P.; Tacke, R. Organometallics 2007, 26, 1295-1298.
5. (b) Doszczak, L.; Kraft, P.; Weber, H.-P.; Bertermann, R.; Triller, A.; Hatt, H.; Tacke, R. Angew. Chem. 2007, 119, 3431-3436;
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7. For an alternative synthesis of 7a, see also: Whitmore, F. C.; Wilson, C. D.; Capinjola, J. V.; Tongberg, C. O.; Fleming, G. H.; McGrew, R. V.; Cosby, J. N. J. Am. Chem. Soc. 1941, 63, 2035-2041.
8. The synthesis of 13 has already been briefly reported, but in order to increase the yield, we improved the described procedure (see: Sommer, L. H.; Goldberg, G. M.; Gold, J.; Whitmore, F. C. J. Am. Chem. Soc 1947, 69, 980)
9. and characterized 13 by NMR spectroscopy. For an alternative synthesis of 13, see also: Sommer, L. H.; Mitch, F. A.; Goldberg, G. M. J. Am. Chem. Soc. 1949, 71, 2746-2750.
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13. To avoid high temperatures, which would cause a partial thermal decomposition of 7c or 7d, both compounds were distilled under mild conditions (0.02 mbar, ≤30 °C).
14. Etzweiler, F.; Senn, E.; Neuner-Jehle, N. Ber. Bunsen-Ges. Phys. Chem. 1984, 88, 578-583.
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16. The PM3 minimum-energy conformers were calculated with the Spartan'04 Macintosh program system; Wavefunction, Inc.: Irvine, CA, 2005. In this context,
17. see also: Hehre, W. J. A Guide to Molecular Mechanics and Quantum Chemical Calculations; Wavefunction, Inc.: Irvine, CA, 2003.
18. Kraft, P.; Bruneau, A. Eur. J. Org. Chem. 2007, 2257-2267.
19. The yield is related to the half-molar equivalent of lithium (62 mmol).