A user-friendly entry to 2-iodoxybenzoic acid (IBX)

Journal of Organic Chemistry

Volumn 64, Issue 12, 1999, Pages 4537-4538

  Frigerio, Marco ^a   Santagostino, Marco ^a   Sputore, Simona ^a  

^a Prassis Sigma Tau Research Institute   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

IODOBENZOIC ACID DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033546262     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9824596     Document Type: Article

References (30)

1. Hartman, C.; Meyer, V. Chem. Ber. 1893, 26, 1727.
2. (a) Dess, B. D.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
3. (b) Dess, B. D.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277 and references therein. Improved protocols for the preparation of 2 from 1 have been reported:
4. (c) Ireland, R. E.; Liu, L. J. J. Org. Chem. 1993, 58, 2899.
5. (d) Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
6. (a) Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
7. (b) Frigerio, M.; Santagostino, M.; Sputore S.; Palmisano, G. J. Org. Chem. 1995, 60, 7272.
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9. For some recent examples, see: Breuilles, P.; Uguen, D. Tetrahedron Lett. 1998, 39, 3149. Varadarajan, S.; Mohapatra, D. K.; Datta, A Tetrahedron Lett. 1998, 39, 1075. Hulme, A. N.; Howells, G. E. Tetrahedron Lett. 1997, 38, 8245. Pearson, W. H.; Clark, R. B. Tetrahedron Lett. 1997, 38, 7669. Andrus, M. B.; Shih, T.-L. J. Org. Chem. 1996, 61, 8780. Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498.
10. For some recent examples, see: Breuilles, P.; Uguen, D. Tetrahedron Lett. 1998, 39, 3149. Varadarajan, S.; Mohapatra, D. K.; Datta, A Tetrahedron Lett. 1998, 39, 1075. Hulme, A. N.; Howells, G. E. Tetrahedron Lett. 1997, 38, 8245. Pearson, W. H.; Clark, R. B. Tetrahedron Lett. 1997, 38, 7669. Andrus, M. B.; Shih, T.-L. J. Org. Chem. 1996, 61, 8780. Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498.
11. For some recent examples, see: Breuilles, P.; Uguen, D. Tetrahedron Lett. 1998, 39, 3149. Varadarajan, S.; Mohapatra, D. K.; Datta, A Tetrahedron Lett. 1998, 39, 1075. Hulme, A. N.; Howells, G. E. Tetrahedron Lett. 1997, 38, 8245. Pearson, W. H.; Clark, R. B. Tetrahedron Lett. 1997, 38, 7669. Andrus, M. B.; Shih, T.-L. J. Org. Chem. 1996, 61, 8780. Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498.
12. For some recent examples, see: Breuilles, P.; Uguen, D. Tetrahedron Lett. 1998, 39, 3149. Varadarajan, S.; Mohapatra, D. K.; Datta, A Tetrahedron Lett. 1998, 39, 1075. Hulme, A. N.; Howells, G. E. Tetrahedron Lett. 1997, 38, 8245. Pearson, W. H.; Clark, R. B. Tetrahedron Lett. 1997, 38, 7669. Andrus, M. B.; Shih, T.-L. J. Org. Chem. 1996, 61, 8780. Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498.
13. For some recent examples, see: Breuilles, P.; Uguen, D. Tetrahedron Lett. 1998, 39, 3149. Varadarajan, S.; Mohapatra, D. K.; Datta, A Tetrahedron Lett. 1998, 39, 1075. Hulme, A. N.; Howells, G. E. Tetrahedron Lett. 1997, 38, 8245. Pearson, W. H.; Clark, R. B. Tetrahedron Lett. 1997, 38, 7669. Andrus, M. B.; Shih, T.-L. J. Org. Chem. 1996, 61, 8780. Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498.
14. For some recent examples, see: Breuilles, P.; Uguen, D. Tetrahedron Lett. 1998, 39, 3149. Varadarajan, S.; Mohapatra, D. K.; Datta, A Tetrahedron Lett. 1998, 39, 1075. Hulme, A. N.; Howells, G. E. Tetrahedron Lett. 1997, 38, 8245. Pearson, W. H.; Clark, R. B. Tetrahedron Lett. 1997, 38, 7669. Andrus, M. B.; Shih, T.-L. J. Org. Chem. 1996, 61, 8780. Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498.
15. Frigerio, M.; Santagostino, M.; Sputore, S. Synlett 1997, 833. Hegde, S. G., Myles D. C. Tetrahedron Lett. 1997, 38, 4329.
16. Frigerio, M.; Santagostino, M.; Sputore, S. Synlett 1997, 833. Hegde, S. G., Myles D. C. Tetrahedron Lett. 1997, 38, 4329.
17. Corey, E. J.; Palani A. Tetrahedron Lett. 1995, 36, 3485. Corey, E. J.; Palani A. Tetrahedron Lett. 1995, 36, 7945.
18. Corey, E. J.; Palani A. Tetrahedron Lett. 1995, 36, 3485. Corey, E. J.; Palani A. Tetrahedron Lett. 1995, 36, 7945.
19. Bose, D. S.; Srinivas, P.; Gurjar, M. K. Tetrahedron Lett. 1997, 38, 5839.
20. Bose, D. S.; Srinivas, P. Synlett 1998, 977.
21. 2/NaOCl: Bell, R.; Morgan, K. J. J. Chem. Soc. 1960, 1209.
22. 2: Katritzky, A. R.; Duell, B. L.; Gallos, J. K. Org. Magn. Reson. 1989, 27, 1007.
23. 4: ref 1.
24. 2: Hartman, C.; Meyer, V. Chem. Ber. 1894, 27, 1600.
25. (a) Greenbaum, F. R. Am. J. Pharm. 1936, 108, 17.
26. (b) Banerjee, A.; Banerjee, G. C.; Bhattacharya, S.; Banerjee, S.; Samaddar, H. J. Ind. Chem. Soc. 1981, 58, 605.
27. 4 procedure, is in press (Boeckman, R. K., Jr.; Shao, P.; Mullins, J. J. Org. Synth.).
28. 2b The purity of the reagent varied between 90 and 95%, the major contaminants being 2-iodobenzoic acid (1-3%) and 2-iodosobenzoic acid (5-10%).
29. Working at higher temperature (95-100 °C) is not advisable since IBX is consistentely reduced to 2-iodosobenzoic acid under these conditions; for the same reason, recrystallization from pure water (at 75 °C, 1.0 g of IBX 98% in 60 mL) is unapplicable since the procedure yields a product (56% yield) of decreased purity (90% of IBX, 7% and 3% of 2-iodoso and 2-iodobenzoic acid, respectively).
30. Plumb, J. B.; Harper, D. J. Chem. Eng. News 1990, July 16, 3.