Odor-structure relationships using fluorine as a probe

Tetrahedron

Volumn 56, Issue 25, 2000, Pages 4253-4260

  Michel, Dominique ^a   Schlosser, Manfred ^a  

^a UNIVERSITY OF LAUSANNE   (Switzerland)

Author keywords

Conformation; Dipole dipole interactions; Epoxides; Olfactory evaluation; Organofluorine compounds

Indexed keywords

ESTER DERIVATIVE; ETHER DERIVATIVE; FLUORINE; HALOGEN; KETONE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONFORMATIONAL TRANSITION; ODOR; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS;

EID: 0034674636     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00351-3     Document Type: Article

References (41)

1. Schlosser M. Soloshonok V.A. Enantiocontrolled Synthesis of Fluoroorganic Compounds: Stereochemical Challenges and Biomedicinal Targets. 1999;613-659 Wiley, Chichester.
2. Schlosser M., Michel D. Tetrahedron. 52:1996;99-108.
3. Bauer K., Garbe D., Surburg H. Common Fragrance and Flavor Materials. 2nd ed. 1990;VCH, Weinheim.
4. Ohloff G. Riechstoffe und Geruchssinn: Die molekulare Welt der Düfte. 1990;Springer, Berlin.
5. Müller P.M., Lamparski D. Perfumes: Art, Science and Technology. 1991;Elsevier, London.
6. Weyerstahl P. J. Prakt. Chem., Chem.-Ztg. 336:1994;95-109.
7. Rossiter K.J. Chem. Rev. 96:1996;3201-3240.
8. Haufe, G.; Alvernhe, G.; Laurent, A. Tetrahedron Lett. 1986, 27, 4449-4452; Alvernhe, G.; Laurent, A.; Haufe, G. Synthesis 1987, 562-564; Alvernhe, G.; Anker, D.; Laurent, A.; Haufe, G.; Béguin, C. Tetrahedron 1988, 44, 3551-3563.
9. Haufe, G.; Alvernhe, G.; Laurent, A. Tetrahedron Lett. 1986, 27, 4449-4452; Alvernhe, G.; Laurent, A.; Haufe, G. Synthesis 1987, 562-564; Alvernhe, G.; Anker, D.; Laurent, A.; Haufe, G.; Béguin, C. Tetrahedron 1988, 44, 3551-3563.
10. Haufe, G.; Alvernhe, G.; Laurent, A. Tetrahedron Lett. 1986, 27, 4449-4452; Alvernhe, G.; Laurent, A.; Haufe, G. Synthesis 1987, 562-564; Alvernhe, G.; Anker, D.; Laurent, A.; Haufe, G.; Béguin, C. Tetrahedron 1988, 44, 3551-3563.
11. Haufe G., Alvernhe G., Laurent A., Ernet T., Goj O., Kröger S., Sattler A. Org. Synth. 76:1999;159-168.
12. Franz R. J. Fluorine Chem. 15:1980;423-434.
13. Suga H., Hamatani T., Guggisberg Y., Schlosser M. Tetrahedron. 46:1990;4255-4260.
14. Matsubara S., Matsuda H., Hamatani T., Schlosser M. Tetrahedron. 44:1988;2855-2863.
15. Suga H., Hamatani T., Schlosser M. Tetrahedron. 46:1990;4247-4254.
16. Nagakura I., Savary D.N.-H., Schlosser M. Helv. Chim. Acta. 63:1980;1257-1263.
17. Michel D., Schlosser M. Tetrahedron. 52:1996;2429-2434.
18. Schlosser M., Michel D., Guo Z.-W., Sih C.J. Tetrahedron. 52:1996;8257.
19. Desponds O., Franzini L., Schlosser M. Synthesis. 1997;150-152.
20. Michel D., Witschard M., Schlosser M. Liebigs Ann. 1997;517-519.
21. Fouquet, G.; Schlosser, M. Angew. Chem. 1974, 86, 50-51; Angew. Chem., Int. Ed. Engl. 1974, 13, 82-82; s.a.: Schlosser, M.; Bossert, H. Tetrahedron 1991, 47, 7323-7328.
22. Fouquet, G.; Schlosser, M. Angew. Chem. 1974, 86, 50-51; Angew. Chem., Int. Ed. Engl. 1974, 13, 82-82; s.a.: Schlosser, M.; Bossert, H. Tetrahedron 1991, 47, 7323-7328.
23. Fouquet, G.; Schlosser, M. Angew. Chem. 1974, 86, 50-51; Angew. Chem., Int. Ed. Engl. 1974, 13, 82-82; s.a.: Schlosser, M.; Bossert, H. Tetrahedron 1991, 47, 7323-7328.
24. Sicher J., Svoboda M., Pánková M., Závada J. Collect. Czech. Chem. Commun. 36:1971;3633-3649.
25. Nozaki H., Noyori R. J. Org. Chem. 30:1962;1652-1654.
26. Dutch Patent 6,411,715 (Cl. C07c, filed on 8 October 1993, issued on 9 April 1965; to Haarmann and Reimer); Chem. Abstr. 1965, 63, 8228b.
27. Kobelt M., Barman P., Prelog V., Ruzicka L. Helv. Chim. Acta. 32:1949;256-265.
28. Vandenheuvel W.J.A., Gardiner W.L., Horning E.C. J. Chromatogr. 19:1965;263-276.
29. Morel, C. Soap, Perfumery & Cosmetics 1950, 23, 732-734; Chem. Abstr. 1950, 44, 11037a.
30. Morel, C. Soap, Perfumery & Cosmetics 1950, 23, 732-734; Chem. Abstr. 1950, 44, 11037a.
31. Svirbely W.J., Eareckson W.M., Matsuda K., Pickard H.B., Solet I.S., Tuemmler W.B. J. Am. Chem. Soc. 71:1949;507-509.
32. Ono N., Yamada T., Saito T., Tanaka K., Kaji A. Bull. Chem. Soc. Jpn. 51:1978;2401-2404.
33. Cheng Y.S., von Rudloff E. Phytochemistry. 9:1970;2517-2527.
34. Gertler, S. I.; Feldmesse, J.; Rebois, R. V. J. Agric. Food Chem. 1958, 6, 843-844; Chem. Abstr. 1959, 53, 15461d; s.a.: Fuji, K.; Node, M.; Kawabata, T.; Fujimoto, M. J. Chem. Soc., Perkin Trans. 1 1987, 1043-1048.
35. Gertler, S. I.; Feldmesse, J.; Rebois, R. V. J. Agric. Food Chem. 1958, 6, 843-844; Chem. Abstr. 1959, 53, 15461d; s.a.: Fuji, K.; Node, M.; Kawabata, T.; Fujimoto, M. J. Chem. Soc., Perkin Trans. 1 1987, 1043-1048.
36. Gertler, S. I.; Feldmesse, J.; Rebois, R. V. J. Agric. Food Chem. 1958, 6, 843-844; Chem. Abstr. 1959, 53, 15461d; s.a.: Fuji, K.; Node, M.; Kawabata, T.; Fujimoto, M. J. Chem. Soc., Perkin Trans. 1 1987, 1043-1048.
37. Ruzicka L., Stoll M., Schinz H. Helv. Chim. Acta. 9:1926;249-264.
38. Nozaki H., Yamamoto H., Mori T. Can J. Chem. 47:1969;1107-1112.
39. Karpf M., Dreiding A.S. Helv. Chim. Acta. 58:1975;2409-2422.
40. Büchi G., Wüest H. Helv. Chim. Acta. 62:1979;2661-2672.
41. Ruzicka L., Schinz H., Pfeifer M. Helv. Chim. Acta. 11:1928;686-700.