Radical-mediated bromination of carbohydrate derivatives: Searching for alternative reaction conditions without carbon tetrachloride

Tetrahedron Letters

Volumn 43, Issue 49, 2002, Pages 8849-8852

  Czifrák, Katalin ^a   Somsák, László ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

Author keywords

Carbohydrates; Halogenation; Radicals and radical reactions; Substitution

Indexed keywords

BROMINE DERIVATIVE; CARBOHYDRATE DERIVATIVE; CARBON TETRACHLORIDE; CHLOROETHANE; FLUORIDE; FUNCTIONAL GROUP; MONOSACCHARIDE; POTASSIUM BROMATE; RADICAL; SODIUM SULFATE; SOLVENT; WATER;

ARTICLE; BROMINATION; ENVIRONMENT; HAZARD; HEALTH HAZARD; REACTION ANALYSIS;

EID: 0037010823     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02205-0     Document Type: Article

References (20)

1. Madsen, R. In Glycoscience; Fraser-Reid, B.; Tatsuta, L.; Thiem, J., Eds. Springer: Berlin, 2001; Vol. I, pp. 215-216.
2. Somsák L., Ferrier R.J. Adv. Carbohydr. Chem. Biochem. 49:1991;37-92.
3. . An alternative to the radical-mediated bromination involves deprotonation of a suitable carbohydrate derivative followed by a reaction with bromine. For some examples, see: Somsák L. Chem. Rev. 101:2001;81-135.
4. Selected examples of carbohydrate products not included in Ref. 2, the preparation of which involves radical-mediated bromination: (a) Ly, H. D.; Howard, S.; Shum, K.; He, S.; Zhu, A.; Withers, S. G. Carbohydr. Res. 2000, 329, 539-547; (b) Kiss, L.; Somsák, L. Carbohydr. Res. 1996, 291, 43-52; (c) Harrington, P.; Jung, M. Tetrahedron Lett. 1994, 35, 5145-5148; (d) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 157-170; (e) Smith, M. D.; Long, D. D.; Martin, A.; Campbell, N.; Blériot, Y.; Fleet, G. W. J. Synlett 1999, 1151-1153; (f) Somsák, L.; Nagy, V. Tetrahedron: Asymmetry 2000, 11, 1719-1727; (g) Praly, J.-P.; Chen, G. R.; Gola, J.; Hetzer, G. Eur. J. Org. Chem. 2000, 2831-2838; (h) Newcombe, N. J.; Mahon, M. F.; Molloy, K. C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430-6431.
5. Selected examples of carbohydrate products not included in Ref. 2, the preparation of which involves radical-mediated bromination: (a) Ly, H. D.; Howard, S.; Shum, K.; He, S.; Zhu, A.; Withers, S. G. Carbohydr. Res. 2000, 329, 539-547; (b) Kiss, L.; Somsák, L. Carbohydr. Res. 1996, 291, 43-52; (c) Harrington, P.; Jung, M. Tetrahedron Lett. 1994, 35, 5145-5148; (d) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 157-170; (e) Smith, M. D.; Long, D. D.; Martin, A.; Campbell, N.; Blériot, Y.; Fleet, G. W. J. Synlett 1999, 1151-1153; (f) Somsák, L.; Nagy, V. Tetrahedron: Asymmetry 2000, 11, 1719-1727; (g) Praly, J.-P.; Chen, G. R.; Gola, J.; Hetzer, G. Eur. J. Org. Chem. 2000, 2831-2838; (h) Newcombe, N. J.; Mahon, M. F.; Molloy, K. C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430-6431.
6. Selected examples of carbohydrate products not included in Ref. 2, the preparation of which involves radical-mediated bromination: (a) Ly, H. D.; Howard, S.; Shum, K.; He, S.; Zhu, A.; Withers, S. G. Carbohydr. Res. 2000, 329, 539-547; (b) Kiss, L.; Somsák, L. Carbohydr. Res. 1996, 291, 43-52; (c) Harrington, P.; Jung, M. Tetrahedron Lett. 1994, 35, 5145-5148; (d) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 157-170; (e) Smith, M. D.; Long, D. D.; Martin, A.; Campbell, N.; Blériot, Y.; Fleet, G. W. J. Synlett 1999, 1151-1153; (f) Somsák, L.; Nagy, V. Tetrahedron: Asymmetry 2000, 11, 1719-1727; (g) Praly, J.-P.; Chen, G. R.; Gola, J.; Hetzer, G. Eur. J. Org. Chem. 2000, 2831-2838; (h) Newcombe, N. J.; Mahon, M. F.; Molloy, K. C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430-6431.
7. Selected examples of carbohydrate products not included in Ref. 2, the preparation of which involves radical-mediated bromination: (a) Ly, H. D.; Howard, S.; Shum, K.; He, S.; Zhu, A.; Withers, S. G. Carbohydr. Res. 2000, 329, 539-547; (b) Kiss, L.; Somsák, L. Carbohydr. Res. 1996, 291, 43-52; (c) Harrington, P.; Jung, M. Tetrahedron Lett. 1994, 35, 5145-5148; (d) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 157-170; (e) Smith, M. D.; Long, D. D.; Martin, A.; Campbell, N.; Blériot, Y.; Fleet, G. W. J. Synlett 1999, 1151-1153; (f) Somsák, L.; Nagy, V. Tetrahedron: Asymmetry 2000, 11, 1719-1727; (g) Praly, J.-P.; Chen, G. R.; Gola, J.; Hetzer, G. Eur. J. Org. Chem. 2000, 2831-2838; (h) Newcombe, N. J.; Mahon, M. F.; Molloy, K. C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430-6431.
8. Selected examples of carbohydrate products not included in Ref. 2, the preparation of which involves radical-mediated bromination: (a) Ly, H. D.; Howard, S.; Shum, K.; He, S.; Zhu, A.; Withers, S. G. Carbohydr. Res. 2000, 329, 539-547; (b) Kiss, L.; Somsák, L. Carbohydr. Res. 1996, 291, 43-52; (c) Harrington, P.; Jung, M. Tetrahedron Lett. 1994, 35, 5145-5148; (d) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 157-170; (e) Smith, M. D.; Long, D. D.; Martin, A.; Campbell, N.; Blériot, Y.; Fleet, G. W. J. Synlett 1999, 1151-1153; (f) Somsák, L.; Nagy, V. Tetrahedron: Asymmetry 2000, 11, 1719-1727; (g) Praly, J.-P.; Chen, G. R.; Gola, J.; Hetzer, G. Eur. J. Org. Chem. 2000, 2831-2838; (h) Newcombe, N. J.; Mahon, M. F.; Molloy, K. C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430-6431.
9. Selected examples of carbohydrate products not included in Ref. 2, the preparation of which involves radical-mediated bromination: (a) Ly, H. D.; Howard, S.; Shum, K.; He, S.; Zhu, A.; Withers, S. G. Carbohydr. Res. 2000, 329, 539-547; (b) Kiss, L.; Somsák, L. Carbohydr. Res. 1996, 291, 43-52; (c) Harrington, P.; Jung, M. Tetrahedron Lett. 1994, 35, 5145-5148; (d) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 157-170; (e) Smith, M. D.; Long, D. D.; Martin, A.; Campbell, N.; Blériot, Y.; Fleet, G. W. J. Synlett 1999, 1151-1153; (f) Somsák, L.; Nagy, V. Tetrahedron: Asymmetry 2000, 11, 1719-1727; (g) Praly, J.-P.; Chen, G. R.; Gola, J.; Hetzer, G. Eur. J. Org. Chem. 2000, 2831-2838; (h) Newcombe, N. J.; Mahon, M. F.; Molloy, K. C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430-6431.
10. Selected examples of carbohydrate products not included in Ref. 2, the preparation of which involves radical-mediated bromination: (a) Ly, H. D.; Howard, S.; Shum, K.; He, S.; Zhu, A.; Withers, S. G. Carbohydr. Res. 2000, 329, 539-547; (b) Kiss, L.; Somsák, L. Carbohydr. Res. 1996, 291, 43-52; (c) Harrington, P.; Jung, M. Tetrahedron Lett. 1994, 35, 5145-5148; (d) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 157-170; (e) Smith, M. D.; Long, D. D.; Martin, A.; Campbell, N.; Blériot, Y.; Fleet, G. W. J. Synlett 1999, 1151-1153; (f) Somsák, L.; Nagy, V. Tetrahedron: Asymmetry 2000, 11, 1719-1727; (g) Praly, J.-P.; Chen, G. R.; Gola, J.; Hetzer, G. Eur. J. Org. Chem. 2000, 2831-2838; (h) Newcombe, N. J.; Mahon, M. F.; Molloy, K. C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430-6431.
11. Selected examples of carbohydrate products not included in Ref. 2, the preparation of which involves radical-mediated bromination: (a) Ly, H. D.; Howard, S.; Shum, K.; He, S.; Zhu, A.; Withers, S. G. Carbohydr. Res. 2000, 329, 539-547; (b) Kiss, L.; Somsák, L. Carbohydr. Res. 1996, 291, 43-52; (c) Harrington, P.; Jung, M. Tetrahedron Lett. 1994, 35, 5145-5148; (d) Brandstetter, T. W.; Wormald, M. R.; Dwek, R. A.; Butters, T. D.; Platt, F. M.; Tsitsanou, K. E.; Zographos, S. E.; Oikonomakos, N. G.; Fleet, G. W. J. Tetrahedron: Asymmetry 1996, 7, 157-170; (e) Smith, M. D.; Long, D. D.; Martin, A.; Campbell, N.; Blériot, Y.; Fleet, G. W. J. Synlett 1999, 1151-1153; (f) Somsák, L.; Nagy, V. Tetrahedron: Asymmetry 2000, 11, 1719-1727; (g) Praly, J.-P.; Chen, G. R.; Gola, J.; Hetzer, G. Eur. J. Org. Chem. 2000, 2831-2838; (h) Newcombe, N. J.; Mahon, M. F.; Molloy, K. C.; Alker, D.; Gallagher, T. J. Am. Chem. Soc. 1993, 115, 6430-6431.
12. Tanko J.M., Blackert J.F. Science (Washington D. C.). 263:1994;203-205.
13. Kikuchi D., Sakaguchi S., Ishii Y. J. Org. Chem. 63:1998;6023-6026.
14. Adinolfi M., Barone G., Guariniello L., Iadonisi A. Tetrahedron Lett. 40:1999;8439-8441.
15. Adinolfi M., Guariniello L., Iadonisi A., Mangoni L. Synlett. 2000;1277-1278.
16. Osz E., Czifrák K., Deim T., Szilágyi L., Bényei A., Somsák L. Tetrahedron. 57:2001;5429-5434.
17. Bedel S., Ulrich G., Piccard C. Tetrahedron Lett. 43:2002;1697-1700.
18. 2 as a reaction medium in various transformations: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531-2532; (b) Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450-451.
19. 2 as a reaction medium in various transformations: (a) Curran, D. P.; Hadida, S. J. Am. Chem. Soc. 1996, 118, 2531-2532; (b) Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450-451.
20. Senni D., Praly J.-P. Synth. Commun. 28:1998;433-441.