Addition reactions of alkenes with electronegatively substituted alcohols in the presence of xenon difluoride

Journal of the Chemical Society. Perkin Transactions 2

Volumn , Issue 4, 1997, Pages 787-794

  Druelinger, Melvin L ^a   Shellhamer, Dale F ^b   Chapman, Robert D ^c,d   Shackelford, Scott A ^c   Riner, Maurice E ^a   Carter, Steven L ^b   Callahan, Ryan P ^b   Youngstrom, Cameron R ^b  

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

^b POINT LOMA NAZARENE UNIVERSITY   (United States)

^c AIR FORCE RESEARCH LABORATORY   (United States)

^d NAVAL AIR WARFARE CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000009863     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a604677k     Document Type: Article

References (31)

1. D. F. Shellhamer, C. M. Curtis, R. H. Dunham, D. R. Hollingsworth, M. L. Ragains, R. E. Richardson, V. L. Heasley, S. A. Shackelford and G. E. Heasley, J. Org. Chem., 1985, 50, 2751.
2. D. F. Shellhamer, S. L. Carter, R. H. Dunham, S. N. Graham, M. P. Spitsbergen, V. L. Heasley, R. D. Chapman and M. L. Druelinger, J. Chem. Soc., Perkin Trans. 2, 1989, 159.
3. (a) M. J. Kamlet, USP 3 541 160/1970;
4. (b) F. E. Martin, USP 3 629 338/1971;
5. (c) H. M. Peters and R. L. Simon, Jr., USP 3 922 311/ 1975.
6. V. V. Avdonin, E. P. Kirpichev, Yu. I. Rubtsov, M. A. Fadeev, G. V. Oreshko and L. T. Eremenko, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1991, 2189.
7. Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, eds. R. Filler, Y. Kobayashi and L. M. Yagupolskii, Elsevier, Amsterdam, 1993.
8. B. K. Park and N. R. Kitteringham, Drug Metab. Rev., 1994, 26, 605.
9. M. Zupan, A. Gregorčič and A. Pollak, J. Org. Chem., 1977, 42, 1562.
10. S. A. Shackelford, J. Org. Chem., 1979, 44, 3485.
11. L. T. Eremenko and F. Ya. Natsibullin, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1968, 875.
12. M. J. Kamlet and H. G. Adolph, J. Org. Chem., 1968, 33, 3073.
13. (a) J. March, Advanced Organic Chemistry, Wiley, New York, 4th edn., 1992, ch. 9, and references therein;
14. (b) T. H. Lowry and K. S. Richardson, Mechanism and Theory in Organic Chemistry, Harper & Row, New York, 3rd edn., 1987, p. 153.
15. C. Hansch, A. Leo and R. W. Taft, Chem. Rev., 1991, 91, 165.
16. (a) T. N. Hall, Tetrahedron, 1963, 19 (Suppl. 1), 115;
17. (b) T. N. Hall, J. Org. Chem., 1964, 29, 3587.
18. V. K. Krylov and I. V. Tselinskii, Org. React. (USSR), 1970, 7, 33.
19. (a) H. S. Booth and D. R. Martin, Boron Trifluoride and Its Derivatives, Wiley, New York, 1949, pp. 176-182;
20. (b) A. V. Topchiev, S. V. Zavgorodnii and Ya. M. Paushkin, Boron Fluoride and Its Compounds as Catalysts in Organic Chemistry, Pergamon Press, New York, 1959, ch. 7.
21. H. G. Adolph, USP 3 962 349/1976.
22. (a) R. R. McGuire, R. E. Cochoy and S. A. Shackelford, USP 4 424 398/1984;
23. (b) R. E. Cochoy, R. R. McGuire and S. A. Shackelford, J. Org. Chem., 1990, 55, 1401;
24. (c) S. A. Shackelford, R. R. McGuire and R. E. Cochoy, J. Org. Chem., 1992, 57, 2950;
25. (d) R. R. McGuire, J. L. Pflug, M. H. Rakowsky, S. A. Shackelford and A. A. Shaffer, Heterocycles, 1994, 38, 1979.
26. H. Feuer, G. Leston, R. Miller and A. T. Nielsen, J. Org. Chem., 1963, 28, 339.
27. (a) M. Eisenberg and D. D. DesMarteau, Inorg. Nucl. Chem. Lett., 1970, 6, 29;
28. (b) K. Seppelt and D. Lentz, Prog. Inorg. Chem., 1982, 29, 167.
29. S. A. Shackelford, R. R. McGuire and J. L. Pflug, Tetrahedron Lett., 1977, 363.
30. R. A. Hildreth, M. L. Druelinger and S. A. Shackelford, Tetrahedron Lett., 1982, 1059. In this paper, product VI is incorrectly displayed; it should be 3-exo-acetamido-2-endo-fluoronorbornane.
31. 1 and 1c, reported herein.