Facile conversion of alcohols into their bromides and iodides by N-bromo and N-iodosaccharins/triphenylphosphine under neutral conditions

Tetrahedron Letters

Volumn 47, Issue 11, 2006, Pages 1771-1775

  Firouzabadi, Habib ^a   Iranpoor, Nasser ^a   Ebrahimzadeh, Farzaneh ^a  

^a SHIRAZ UNIVERSITY   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; BROMINE DERIVATIVE; IODINE DERIVATIVE; N BROMOSACCHARIN DERIVATIVE; N IODOSACCHARIN DERIVATIVE; SACCHARIN DERIVATIVE; TRIPHENYLPHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ROOM TEMPERATURE; SYNTHESIS;

EID: 32244442226     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.01.033     Document Type: Article

References (44)

1. R.D. Chambers, and S.R. James D.H.R. Barton W.D. Ollis Comprehensive Organic Chemistry Vol. 1 1979 Pergamon Press Oxford 493
2. R. Bohlmann B.M. Trost I. Fleming Comprehensive Organic Synthesis Vol. 6 1991 Pergamon Press Oxford 203 223
3. M. Hudlicky, and T. Hudlicky S. Patai Z. Rappoport Chemistry of Functional Groups, Supplement D 1983 Wiley New York 1021
4. Y. Kita, K. Gotanda, A. Sano, M. Oka, K. Murata, M. Suemura, and M. Matsugi Tetrahedron Lett. 48 1997 8345 8348
5. Y. Kita, A. Sano, T. Yamaguchi, M. Oka, K. Gotanda, and M. Matsugi Tetrahedron Lett. 38 1997 3549 3552
6. Y. Kita, A. Sano, T. Yamaguchi, M. Oka, K. Gotanda, and M. Matsugi J. Org. Chem. 64 1999 675 678
7. Y. Kita, H. Nambu, N.G. Ramesh, G. Antikumar, and M. Matsugi Org. Lett. 3 2001 1157 1160
8. (e) Kita, Y.; Matsugi, M. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim; Vol. 1, p 1.
9. S.P. Marsden Contemp. Org. Synth. 4 1997 118 and references cited therein
10. H. Firouzabadi, N. Iranpoor, and M. Jafarpour Tetrahedron Lett. 45 2004 7451 7454
11. N. Iranpoor, H. Firouzabadi, A. Jamalian, and F. Kazemi Tetrahedron 61 2005 5699 5704
12. O. Mitsunobu Synthesis 1981 1 28
13. P.T. Ho, and N. Davies J. Org. Chem. 49 1984 3027 3029
14. Fluka's Chemika News October 2001 lists DEAD as 'temporarily not available because of a reclassification of DEAD explosion risks' L.D. Arnold, H.I. Assil, and J.C. Vederas Org. Synth. 73 1995 278
15. R.K. Boeckman Jr., and B. Ganem Tetrahedron Lett. 15 1974 913 916
16. B. Classon, and Z. Liu J. Org. Chem. 53 1988 6126 6130
17. G.A. Wiley, R.L. Hershkowitz, B.M. Rein, and B.C. Chung J. Am. Chem. Soc. 86 1964 964 965
18. I. Tomoskozi, L. Gruber, and L. Radics Tetrahedron Lett. 16 1975 2473 2476
19. A.J. Burn, and J.I.G. Cadogan Organophosphorus Compd. 17 1963 5788 5796
20. J. Hooz, and S.S.H. Gilani Can. J. Chem. 46 1968 86 87
21. J.P.H. Verheyden, and J.G. Moffatt J. Org. Chem. 37 1972 2289 2299
22. T. Oshikawa, and M. Yamashita Bull. Chem. Soc. Jpn. 57 1984 2675
23. A. Tanaka, and T. Oritani Tetrahedron Lett. 38 1997 1955 1957
24. N. Iranpoor, H. Firouzabadi, Gh. Aghapour, and A.R. Vaezzadeh Tetrahedron 58 2002 8689 8693
25. T. Tsunoda, Y. Yamamiya, and Sh. Itôt Tetrahedron Lett. 34 1993 1639 1642
26. http://ptcl.phys.chem.ox.ac.uk/MSDS/TR/tributylphosphine.html.
27. S.C. Virgil A.J. Pearson W.J. Roush Handbook of Reagents for Organic Synthesis. Activating and Protecting Groups Vol. 4 1999 John Wiley & Sons Ltd New York 438 440
28. A.K. Bose, and B. Lal Tetrahedron Lett. 40 1973 3937 3940
29. O. Sugimoto, M. Mori, and K. Tanji Tetrahedron Lett. 40 1999 7477 7478
30. S. Trippett J. Chem. Soc. 1962 2337 2340
31. I.S. Heilbron, J.H. Emeleus, H.W. Melville, and A.R. Todd Thorpe's Dictionary of Applied Chemistry, 4th ed. Vol. 10 1952 pp 647-651 and references cited therein
32. J.M. Bachhawat, and N.K. Mathur Indian J. Chem. 9 1971 1335 1336
33. V. Manoharan, and N. Venkatasubramanian J. Indian Chem. Soc. 63 1986 613 615
34. I. Možek, and B. Šket Synth. Commun. 22 1992 2513 2520
35. S.P.L. Souza, J.F.M. Silva, and M.C.S. Mattos J. Braz. Chem. Soc. 14 2003 832 835
36. D. Dolenc Synth. Commun. 33 2003 2917 2924
37. P. Anandasundaresan, V.S. Panchatsharam, K. Nagarajan, V. Balasubramanian, and N. Venkatasubramanian Indian J. Chem. 19A 1980 576 578
38. E.I. Sanchez, and M.J. Fumarola J. Org. Chem. 47 1982 1588 1590
39. D. Dolenc Synlett 2000 544 546
40. S. Soraia, S. Jaoquim, and D. Marco Synth. Commun. 33 2003 935 939 and references cited therein
41. M.J. Aloui, and A. Fairbanks Synlett 2001 797 799
42. A.A. Gakh, S.V. Romaniko, B.I. Ugrak, and A.A. Fainziberg Tetrahedron 47 1991 7447 7458
43. E.I. Sanchez, and M.J. Fumarola Synthesis 1976 736 737
44. D. Dolenc, and B. Šket Synlett 1995 327 328