Nucleophilic substitution reactions of N-alkoxyimidoyl fluorides by carbon nucleophiles

Canadian Journal of Chemistry

Volumn 85, Issue 11, 2007, Pages 913-922

  Dolliver, Debra D ^a   Delatte, David B ^a   Linder, Derek B ^a   Johnson, James E ^b   Canesco, Diana C ^b   Rowe, Jeffrey E ^c  

^a SOUTHEASTERN LOUISIANA UNIVERSITY   (United States)

^b TEXAS WOMAN'S UNIVERSITY   (United States)

^c LA TROBE UNIVERSITY   (Australia)

Author keywords

Carbon acid; Enolate ion substitution; Grignard substitution; Imine enamine tautomerizm; N alkoxyimidoyl fluoride

Indexed keywords

CARBON; DISSOCIATION; GEOMETRY; NUCLEOPHILES; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CARBON ACIDS; ENOLATE ION SUBSTITUTION; GRIGNARD SUBSTITUTION; IMINE ENAMINE TAUTOMERIZM;

NITROGEN COMPOUNDS;

EID: 38149107519     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V07-097     Document Type: Article

References (42)

1. (a) S. Fustero, B. Pina, and A. Simon-Fuentes. Tetrahedron Lett. 38, 6771, (1997);
2. (b) S. Fustero, B. Pina, M. Garcia de la Torre, A. Navarro, C. Ramirez de Arellano, and A. Simon. Org. Lett. 1, 977, (1999);
3. (c) R. Ta-Shma and Z. Rappoport. J. Am. Chem. Soc. 99, 1845, (1977);
4. (d) R. Ta-Shma and Z. Rappoport. J. Am. Chem. Soc. 98, 8460, (1976).
5. (a) J.E. Rowe and K. Lee. Aust. J. Chem. 50, 849, (1997);
6. (b) J.E. Rowe and D.A. Papanelopoulos. Aust. J. Chem. 48, 2041, (1995);
7. (c) J.E. Rowe and A.F. Hegarty. J. Org. Chem. 49, 3083, (1984).
8. (a) J.E. Johnson, D.D. Dolliver, L. Yu, D.C. Canseco, M.A. McAllister, and J.E. Rowe. J. Org. Chem. 69, 2741, (2004);
9. (b) J.E. Johnson, A. Ghafouripour, M. Arfan, and S.L. Todd, D. Sitz. J. Org. Chem. 50, 3348, (1985).
10. (a) D. Enders and U. Reinhold. Tetrahedron: Asymmetry, 8, 1895, (1997);
11. (b) R. Bloch. Chem. Rev. 98, 1407, (1998).
12. (a) C.J. Moody. Chem.Commun. 1341, (2004);
13. (b) C.J. Moody, P.T. Gallagher, A.P. Lightfoot, and A.M.Z. Slawin. J. Org. Chem. 64, 4419, (1999);
14. (c) R.K. Dieter and R. Datar. Can. J. Chem. 71, 814, (1993).
15. (a) K.G. Watson, R.N. Brown, R. Cameron, D.K. Chalmers, S. Hamilton, B. Jin, G.Y. Krippner, A. Luttick, D.B. McConnell, P.A. Reece, J. Ryan, P.C. Stanislawski, S.P. Tucker, W.-Y. Wu, D.L. Barnard, and R.W. Sidwell. J. Med. Chem. 46, 3181, (2003);
16. (b) A. Palani, S. Shapiro, H. Josien, T. Bara, J.W. Clader, W.J. Greenlee, K. Cox, J.M. Strizki, and B.M. Baroudy. J. Med. Chem. 45, 3143, (2002);
17. (c) A. Rossello, S. Bertini, A. Lapucci, M. Macchia, A. Martinelli, S. Rapposelli, E. Herreros, and B. Macchia. J. Med. Chem. 45, 4903, (2002);
18. (d) P.L. Ferrarini, C. Mori, M. Badawneh, V. Calderone, R.Greco, C. Manera, A. Martinelli, P. Nieri, and G. Saccomanni. Eur. J. Med. Chem. 35, 815, (2000);
19. (e) A. Karakurt and S. Dalkara. FABAD J. Pharm. Sci. 24, 143 (1999).
20. (a) E. Fontaine, C. Namane, J. Meneyrol, M. Geslin, L. Serva, E. Roussey, S. Tissandie, M. Maftouh, and P. Roger. Tetrahedron: Asymmetry, 12, 2185, (2001);
21. (b) C. Bolm and M. Felder. Synlett, 655 (1994);
22. (c) Y. Sakito, Y. Yoneyoshi, and G. Suzukamo. Tetrahedron Lett. 29, 223, (1988).
23. (a) E. Abele, R. Abele, J. Popelis, and E. Lukevics. Org. Prep. Proced. Int. 32, 153, (2000);
24. (b) P.E. Titus, P.A. Forte, and J.M. Prokipcak. Can. J. Chem. 54, 647, (1976);
25. (c) R. Andrisano, A.S. Angeloni, F. Del Moro, and M. Tramontini. M. Ann. Chim. (Rome), 55, 645, (1965).
26. (a) J. Skerzewski. Tetrahedron 45, 4593, (1989);
27. (b) G.R. Newkome and G.R. Baker. Org. Prep. Proced. Int. 18, 117, (1986).
28. J.R. Jones. The ionization of carbon acids. Academic Press, New York, 1973.
29. J.P. Guthrie. Can. J. Chem. 45, 4593, (1979).
30. rd Ed. Harper and Rowe: New York. 1987. p. 297.
31. (a) P. Gilli, V. Bertolasi, V. Ferretti, and G. Gilli. J. Am. Chem. Soc. 122, 10405, (2000);
32. (b) V.F. Traven, V.V. Negrebetsky, L.I. Vorobjeva, and E.A. Carberry. Can. J. Chem. 75, 377, (1997);
33. (c) K. Neuvonen, C. Zewi, and H. Lonnberg. Acta Chem. Scand. 50, 1137, (1996);
34. (d) G. Bartoli, C. Cimarelli, T. Calpozzo, and G. Palmieri. Tetrahedron, 51, 8613, (1995);
35. (e) K. Takagi, A. Bajnati, and M.J. Hubert-Habart. Heterocycl. Chem. 31, 973, (1994);
36. (f) A. Arnold, M. Budeshisky, and M. Pankova. Collect. Czech. Chem. Commun. 56, 1019, (1991);
37. (g) A.S. Shawali, N.M. Harb, and K.O. Badahdah. Heterocycl. Chem. 22, 1397, (1985).
38. J.E. Johnson, D.C. Canseco, D.D. Dolliver, J.E. Rowe, and F.R. Fronczek. J. Chem. Cryst. 36, 667, (2006).
39. H. Baba, I. Hori, T. Hayashi, and H. Midorikawa. Bull. Chem. Soc. Jpn. 42, 1653, (1969).
40. J. Pornet and L. Miginiac. Bull. Soc. Chim. Fr. 7-8, 1849, (1975).
41. J.E. Rowe, K. Lee, D.D. Dolliver, and J.E. Johnson. Aust. J. Chem. 52, 807, (1999).
42. X. Creary, Y.-X. Wang, and Z. Jiang. J. Am. Chem. Soc. 117, 3044, (1995).