Design of thermally stable versions of the burgess reagent: Stability and reactivity study (1)

Journal of Organic Chemistry

Volumn 75, Issue 10, 2010, Pages 3447-3450

  Metcalf, Thomas A ^a   Simionescu, Razvan ^a   Hudlicky, Tomas ^a  

^a BROCK UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

OXIRANES; THERMAL STABILITY; THERMALLY STABLE;

SULFUR COMPOUNDS; SYNTHESIS (CHEMICAL); THERMOGRAVIMETRIC ANALYSIS;

THERMODYNAMIC STABILITY;

1,2 EPOXY 3 BUTENE; EPOXIDE; PHOSPHOLIPID; REAGENT;

ARTICLE; CONTROLLED STUDY; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THERMOSTABILITY;

MOLECULAR STRUCTURE; STEREOISOMERISM; SULFONAMIDES; TEMPERATURE;

EID: 77952495808     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo100212n     Document Type: Article

References (26)

1. Presented in part at the 92nd CSC conference in Hamilton, ON, May 2009.
2. Atkins, G. M.; Burgess, E. M. J. Am. Chem. Soc. 1968, 90, 4744
3. Burgess, E. M.; Penton, H. R.; Taylor, E. A. J. Am. Chem. Soc. 1970, 92, 5224
4. Atkins, G. M.; Burgess, E. M. J. Am. Chem. Soc. 1972, 94, 6135
5. Burgess, E. M.; Penton, H. R.; Taylor, E. A. J. Org. Chem. 1973, 38, 26
6. Reviews of applications: Santra, S. Synlett 2009, 852
7. Nicolaou, K. C.; Snyder, S. A.; Longbottom, D. A.; Nalbandian, A. Z.; Huang, X. Chem.-Eur. J. 2004, 10, 5581
8. Khapli, S.; Dey, S.; Mal, D. J. Ind. Inst. Sci. 2001, 81, 461
9. Burckhardt, S. Synlett 2000, 559
10. Lamberth, C. J. Prakt. Chem. 2000, 342, 518
11. Taibe, P.; Mobashery, S. In Encyclopedia of Reagents in Organic Synthesis; Paquette, L. A., Ed.; Wiley: Chichester, UK, 1995; Vol. 5, p 3345.
12. Use in natural product synthesis: Cedrene: Rigby, J. H.; Kirova-Snover, M. Tetrahedron Lett. 1997, 38, 8153
13. Narciclasine: Rigby, J. H.; Mateo, M. E. J. Am. Chem. Soc. 1997, 119, 12655
14. Taxol: Holton, R. A.; Kim, H. B.; Sonoza, C.; Liang, F.; Biediger, R. J.; Boatman, P. D.; Shindo, M.; Smith, C. C.; Kim, S.; Nadizadeh, H.; Suzuki, Y.; Tao, C.; Vu, P.; Tang, S.; Zhang, P.; Murthi, K. K.; Gentile, L. N.; Liu, J. H. J. Am. Chem. Soc. 1994, 116, 1599
15. Efrotomycin: Dolle, R. E.; Nicolaou, K. C. J. Am. Chem. Soc. 1985, 107, 1691
16. Pravastatin: Daniewski, A. R.; Wovkulich, P. M.; Uskokovic, M. R. J. Org. Chem. 1992, 57, 7133
17. Balanol: see ref (7).
18. Rinner, U.; Adams, D. R.; dos Santos, M. L.; Hudlicky, T. Synlett 2003, 1247-1252
19. Nicolaou, K. C.; Snyder, S. A.; Nalbandian, A. Z.; Longbottom, D. A. J. Am. Chem. Soc. 2004, 126, 6234
20. Nicolaou, K. C.; Huang, X.; Snyder, S. A.; Rao, P. B.; Bella, M.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834
21. Nicolaou, K. C.; Longbottom, D. A.; Snyder, S. A.; Nalbandian, A. Z.; Huang, X. Angew. Chem., Int. Ed. 2002, 41, 3866
22. Leisch, H.; Saxon, R.; Sullivan, B.; Hudlicky, T. Synlett 2006, 445-449
23. Sullivan, B.; Gilmet, J.; Leisch, H.; Hudlicky, T. J. Nat. Prod. 2008, 71, 346-350
24. Banfield, S. C.; Omori, A. T.; Leisch, H.; Hudlicky, T. J. Org. Chem. 2007, 72, 4989-4992
25. Leisch, H.; Sullivan, B.; Fonovic, B.; Dudding, T.; Hudlicky, T. Eur. J. Org. Chem. 2009, 2806-2819
26. Burgess, E. M.; Penton, H. R.; Taylor, E. A. J. Org. Chem. 1973, 38, 26-31