Hindered ester formation by SN2 azidation of N-acetoxy-N-alkoxyamides and N-alkoxy-N-chloroamides—novel application of HERON rearrangements

Journal of the Chemical Society. Perkin Transactions 2

Volumn 2, Issue 10, 2002, Pages 1728-1739

  Glover, Stephen A ^a   Mo, Guoning ^a  

^a UNIVERSITY OF NEW ENGLAND   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONITRILE; CHEMICAL REACTIONS; CHLORINE COMPOUNDS; COMPUTER SIMULATION; DECOMPOSITION; ESTERS; MATHEMATICAL MODELS; NITROGEN; PHASE TRANSITIONS; SODIUM COMPOUNDS;

ACETOXYALKOXYAMIDES; ALKOXYCHLOROAMIDES; AZIDATION; HINDERED ESTER FORMATION;

ORGANIC COMPOUNDS;

EID: 0036026293     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/b111250n     Document Type: Article

References (45)

1. S. A. Glover Tetrahedron 1998 54 7229 Tetrahedron Report 455.
2. S. Glover, A. Rauk J. Org. Chem. 1999 64 2340.
3. S. A. Glover, G. Mo, A. Rauk Tetrahedron 1999 55 3413.
4. S. A. Glover, G. Mo, A. Rauk, D. Tucker, P. Turner J. Chem. Soc., Perkin Trans. 2 1999 2053.
5. S. A. Glover, A. Rauk J. Org. Chem. 1996 61 2337.
6. J. M. Buccigross, S. A. Glover, G. P. Hammond Aust. J. Chem. 1995 48 353.
7. J. M. Buccigross, S. A. Glover J. Chem. Soc., Perkin Trans. 2 1995 595.
8. J. J. Campbell, S. A. Glover J. Chem. Res. (S) 1999 8 474 J. Chem. Res. (M) 2075 2096.
9. J. J. Campbell, S. A. Glover J. Chem. Soc., Perkin Trans. 2 1992 1661.
10. M. V. De Almeida, D. H. R. Barton, I. Bytheway, J. A. Ferriera, M. B. Hall, W. Liu, D. K. Taylor, L. Thomson J. Am. Chem. Soc. 1995 117 4870.
11. J. J. Campbell, S. A. Glover, G. P. Hammond, C. A. Rowbottom J. Chem. Soc., Perkin Trans. 2 1991 2067.
12. A. M. Bonin, S. A. Glover, G. P. Hammond J. Chem. Soc., Perkin Trans. 2 1994 1173.
13. A. M. Bonin, S. A. Glover, G. P. Hammond J. Org. Chem. 1998 63 9684.
14. M. Adams, S. A. Glover, and D. J. Tucker, 2001.
15. S. A. Glover and A. Rauk J. Chem. Soc., Perkin Trans. 2, 2002, DOI: 10.1039/b204232k.
16. P. v. R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van Eikema Hommes J. Am. Chem. Soc. 1996 118 6317.
17. G. Mo Properties and Reactions of Anomeric Amides, Ph.D., University of New England, 1999.
18. M. Novak, M. J. Kahley, J. Lin, S. A. Kennedy, L. A. Swanegan J. Am. Chem. Soc. 1994 116 11626.
19. S. A. Kennedy, M. Novak, B. A. Kolb J. Am. Chem. Soc. 1997 119 7654.
20. M. Novak, L. L. Xu, R. A. Wolf J. Am. Chem. Soc. 1998 120 1643.
21. J. C. Fishbein, R. A. McClelland J. Am. Chem. Soc. 1987 109 2824.
22. R. A. Davidse, M. J. Kahley, R. A. McClelland, M. Novak J. Am. Chem. Soc. 1994 116 4513.
23. R. A. McClelland, P. A. Davidse, G. Hadzialic J. Am. Chem. Soc. 1995 117 4173.
24. R. A. McClelland, M. J. Kahley, P. A. Davidse, G. Hadzialic J. Am. Chem. Soc. 1996 118 4794.
25. J. Johns, Synthesis and Thermal Decomposition of N, N-dialkoxybenzamides, Honours thesis, University of New England, 1996.
26. I. O. Sutherland Comprehensive Organic Chemistry, ed. I. O. Sutherland Pergamon Press, Oxford 1979 871.
27. J. Mulzer Comprehensive Organic Synthesis, ed. B. M. Trost Pergamon Press, Oxford 1991 323.
28. J. Mulzer Comprehensive Organic Functional Group Transformations, ed. C. J. Moody Pergamon, Oxford 1995.
29. R. C. Parish, L. M. Stock J. Org. Chem. 1965 30 927.
30. E. M. Kaiser, R. A. Woodruff J. Org. Chem. 1970 35 1198.
31. R. A. Rossi, R. H. de Rossi J. Org. Chem. 1974 39 855.
32. S. Takimoto, J. Inanaga, T. Katsuki, M. Yamagughi Bull. Chem. Soc. Jpn. 1976 49 2335.
33. S. Masamune, Y. Hayase, W. Schilling, W. K. Chan, G. S. Bates J. Am. Chem. Soc. 1977 99 6756.
34. S. Kim, J. I. Lee J. Org. Chem. 1984 49 1712.
35. SPARTAN, Version 5 and MacSPARTAN Pro, Verson 1.0.2, Wavefunction, Inc., 18401 Van Karman Avenue, Suite 370, Irvine, CA 92612 USA.
36. A. D. Becke Phys. Rev. A 1988 38 3098.
37. J. P. Perdew Phys. Rev. B 1986 33 8822.
38. W. J. Hehre, J. Yu, P. E. Klunzinger and L. Lou A Brief Guide to Molecular Mechanics and Quantum Chemical Calculations, Wavefunction, Inc., Irvine, 1998.
39. C. J. Cramer, D. G. Truhlar J. Comp. Aid. Mol. Design 1992 6 69.
40. R. G. Gerdes, S. A. Glover, J. F. Ten Have, C. A. Rowbottom Tetrahedron Lett. 1989 30 2649.
41. T. Koenig, M. Deinver, J. A. Hoobler J. Am. Chem. Soc. 1971 93 938.
42. J. H. Cooley, W. D. Bills, J. R. Throckmorton J. Org. Chem. 1960 25 1734.
43. Organic Synthesis Col. Vol. II, Ed. A. H. Blatt John Wiley and Sons, New York, 1957 67.
44. M. J. Mintz, C. Walling Org. Synth. 1963 49 9.
45. A. J. Clark, J. L. Peacock Tetrahedron Lett. 1998 39 6029.