Facile addition of poorly nucleophilic alcohols to unactivated alkenes

Synthesis

Volumn , Issue 9, 1997, Pages 1056-1060

  Shellhamer, Dale F ^a   Callahan, Ryan P ^a   Heasley, Victor L ^a   Druelinger, Melvin L ^b   Chapman, Robert D ^c  

^a POINT LOMA NAZARENE UNIVERSITY   (United States)

^b Malik and Seeme Hasan School of Business   (United States)

^c NAVAL AIR WARFARE CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

NORBORNANE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030847764     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1313     Document Type: Article

References (36)

1. Patai, S.; Rappoport, Z. In The Chemistry of Alkenes; Patai, S., Ed.; Interscience: London, 1964; Chapter 8.
2. Bernasconi, C. F. Tetrahedron 1989, 45, 4017.
3. Booth, H. S.; Martin, D. R. Boron Trifluoride and Its Derivatives; John Wiley: New York, 1949; pp 176-182.
4. Topchiev, A. V.; Zavgorodnii, S. V.; Paushkin, Ya. M. Boron Fluoride and Its Compounds as Catalysts in Organic Chemistry; Pergamon; New York, 1959; Chapter 7.
5. Adolph, H. G. U. S. Patent 3962349, 1976; Chem. Abstr. 1976, 85, 62649.
6. Cochoy, R. E.; McGuire, R. R.; Shackelford, S. A. J. Org. Chem. 1990, 55, 1401.
7. Hall, T. N. Tetrahedron 1963, 19(Suppl. 1), 115. Hall, T. N. J. Org. Chem. 1964, 29, 3587.
8. Hall, T. N. Tetrahedron 1963, 19(Suppl. 1), 115. Hall, T. N. J. Org. Chem. 1964, 29, 3587.
9. Krylov, V. K.; Tselinskii, I. V. Org. React. (USSR) 1970, 7, 33.
10. Feuer, H.; Leston, G.; Miller, R.; Nielsen, A. T. J. Org. Chem. 1963, 28, 339.
11. Archibald, T. G.; Baum, K. J. Org. Chem. 1990, 55, 3562.
12. Grakauskas, V.; Baum, K. J. Org. Chem. 1969, 34, 3927.
13. Chapman, R. D.; Andreshak, J. L.; Shackelford, S. A. J. Org. Chem. 1988, 53, 3771.
14. Kamlet, M. J. U. S. Patent 3541160, 1970; Chem. Abstr. 1971, 74, 31539.
15. Martin, F. E. U. S. Patent 3629338, 1971; Chem. Abstr. 1972, 76, 58982.
16. Peters, H. M.; Simon, Jr., R. L. U. S. Patent 3922311, 1975; Chem. Abstr. 1976, 84, 121109.
17. Avdonin, V. V.; Kirpichev, E. P.; Rubtsov, Yu. I.; Fadeev, M. A.; Oreshko, G. V.; Eremenko, L. T. Bull. Acad. Sci. USSK, Div. Chem. Sci. 1991, 2189.
18. Filler, R.; Kobayashi, Y.; Yagupolskii, L. M., Eds. Organo-fluorine Compounds in Medicinal Chemistry and Biomedical Applications; Elsevier; Amsterdam, 1993.
19. Park, B. K.; Kitteringham, N. R. Drug Metab. Rev. 1994, 26, 605.
20. Shellhamer, D. F.; Carter, S. L.; Dunham, R. H.; Graham, S. N.; Spitsbergen, M. P.; Heasley, V. L.; Chapman, R. D.; Druelinger, M. L. J. Chem. Soc. Perkin Trans. 2 1989, 159.
21. Druelinger, M. L.; Shellhamer, D. F.; Chapman, R. D.; Shackelford, S. A.; Riner, M. E.; Carter, S. L.; Callahan, R. P.; Youngstrom, C. R. J. Chem. Soc. Perkin Trans. 2 1997, 787.
22. Poon, H. L.; Satchell, D. P. N. J. Chem. Soc. Perkin Trans. 2 1984, 1083.
23. Poon, H. L.; Satchell, D. P. N. J. Chem. Res. (S) 1984, 90.
24. Leone, R. E.; Schleyer, P. von R. Angew. Chem. 1970, 82, 889; Angew. Chem. Int. Ed. Engl. 1970, 9, 860.
25. Leone, R. E.; Schleyer, P. von R. Angew. Chem. 1970, 82, 889; Angew. Chem. Int. Ed. Engl. 1970, 9, 860.
26. Ahlberg, P.; Jonsäll, G.; Engdahl, C. Adv. Phys. Org. Chem. 1983, 19, 223.
27. Bruson, H. A.; Riener, T. W. J. Am. Chem. Soc. 1945, 67, 723.
28. Bruson, H. A. U. S. Patent 2411516, 1946; Chem. Abstr. 1947, 41, 4806.
29. Bruson, H. A.; Riener, T. W. J. Am. Chem. Soc. 1946, 68, 8.
30. Bartlett, P. D.; Schneider, A. J. Am. Chem. Soc. 1946, 68, 6.
31. Feuer, H.; Kucera, T. J. J. Org. Chem. 1960, 25, 2069.
32. Shellhamer, D. F.; Curtis, C. M.; Dunham, R. H.; Hollingsworth, D. R.; Ragains, M. L.; Richardson, R. E.; Heasley, V. L.; Shackelford, S. A.; Heasley, G. E. J. Org. Chem. 1985, 50, 2751, and references therein.
33. Jensen, F. R.; Miller, J. J.; Cristol, S. J.; Beckley, R. S. J. Org. Chem. 1972, 37, 4341.
34. The gas-phase spectrum is similar to that as neat liquid: Hückel, W.; Vogt, O. Justus Liebigs Ann. Chem. 1966, 695, 16.
35. Kirmse, W.; Siegfried, R. Chem. Ber. 1972, 105, 2754.
36. Schneider, H.-J.; Busch, R. J. Org. Chem. 1982, 47, 1766.