Tetrabromo hydrogenated cardanol: Efficient and renewable brominating agent

Organic Letters

Volumn 8, Issue 19, 2006, Pages 4291-4293

  Attanasi, Orazio A ^a   Berretta, Stefano ^a   Favi, Gianfranco ^a   Filippone, Paolino ^a   Mele, Giuseppe ^b   Moscatelli, Giada ^a   Saladino, Raffaele ^c  

^a UNIVERSITY OF URBINO   (Italy)

^b UNIVERSITY OF SALENTO   (Italy)

^c UNIVERSITY OF TUSCIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BROMINE; CARDANOL; HYDROGEN; PHENOL DERIVATIVE;

ARTICLE; CHEMISTRY;

BROMINE; HYDROGEN; PHENOLS;

EID: 33749027191     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061637b     Document Type: Article

References (60)

1. Tyman, J. H. P. Synthetic and Natural Phenols; Elsevier: Amsterdam, 1966 and references therein.
2. Attanasi, O. A.; Buratti, S.; Filippone, P. Chim. Ind. (Milan) 2003, 85, 11.
3. Paramashivappa, R.; Kumar, P. P.; Vithayathil, P. J.; Rao, A. S. J. Agric. Food Chem. 2001, 49, 2548.
4. (a) Sethi, S. C.; Subba Rao, B. C. Indian J. Technol. 1963, 1, 218.
5. (b) Attanasi, O. A.; Buratti, S.; Filippone, P. Org. Prep. Proced. Int. 1995, 27, 645.
6. (c) Lubi, M. C.; Thachil, E. T. Des. Monomers Polym. 2000, 3, 123.
7. (d) Shikha, S.; Bajpayee, M.; Kamani, P. K. Paintindia 2003, 53, 41.
8. Oltremare SpA, Bologna (Italy).
9. Amorati, R.; Attanasi, O. A.; El Ali, B. G.; Filippone, P.; Mele, G.; Spadavecchia, J.; Vasapollo, G. Synthesis 2002, 18, 2749.
10. Attanasi, O. A.; Berretta, S.; Fiani, C.; Filippone, P.; Mele, G.; Saladino, R. Tetrahedron 2006, 62, 6113.
11. Attanasi, O. A.; Ciccarella, G.; Filippone, P.; Mele, G.; Spadavecchia, J.; Vasapollo, G. J. Porphyrins Phthalocyanines 2003, 7, 52.
12. (a) Attanasi, O. A.; Del Sole, R.; Filippone, P.; Mazzetto, S. E.; Mele, G. J.; Vasapollo, G. J. Porphyrins Phthalocyanines 2003, 7, 52.
13. (b) Attanasi, O. A.; Del Sole, R.; Garcìa-Lòpez, E.; Mazzetto, S. E.; Filippone, P.; Mele, G.; Palmisano, L.; Vasapollo, G. Green Chem. 2004, 6, 604.
14. Attanasi, O. A.; Del Sole, R.; Filippone, P.; Ianne, R.; Mazzetto, S. E.; Mele, G.; Vasapollo, G. Synlett 2004, 5, 799.
15. (a) Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum: New York, 1990.
16. (b) March, J. Advanced Organic Chemistry: Reactions, Mechanism and Structure, 4th ed; John Wiley & Sons: New York, 1992.
17. (a) Muathen, H. A. J. Org. Chem. 1992, 57, 2740.
18. (b) Katritzky, A. R.; Li, J.; Stevens, C. V.; Ager, D. J. Org. Prep. Proced. Int. 1994, 26, 439.
19. (c) Conte, V.; DiFuria, F.; Moro, S. Tetrahedron Lett. 1994, 45, 7429.
20. (d) Dinesh, C. U.; Kumar, R.; Pandey, B.; Kumar, P. J. Chem. Soc., Chem. Commun. 1995, 611.
21. (e) Smith, K.; Bahzad, D. Chem. Commun. 1996, 467.
22. (f) Srivastava, S. K.; Chauhan, P. M. S.; Bhaduri, A. P. Chem. Commun. 1996, 2679.
23. (g) Clark, J. H.; Ross, J. C.; Macquarrie, D. J.; Barlow, S. J.; Bastock, T. W. Chem. Commun. 1997, 1203.
24. (h) Barhata, N. B.; Gajare, A. S.; Wakharkar, R. D.; Bedekar, A. B. Tetrahedron Lett. 1998, 39, 6349.
25. (i) Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999.
26. Butler, A.; Walker, J. V. Chem. Rev. 1993, 93, 1937.
27. (a) Bigelow, L. A.; Hanslick, R. S. Org. Synth. Collect.; Wiley: New York, 1943; Vol. 2, p 244.
28. (b) Dowd, P.; Kaufman, C.; Kaufman, P. J. Org. Chem. 1985, 50, 882.
29. (c) Ogilvie, W.; Rank, W. Can. J. Chem. 1987, 65, 166.
30. (d) Hakam, K.; Thielmann, M.; Thielmann, T.; Winterfeldt, E. Tetrahedron 1987, 43, 2035.
31. (e) Jana, N. K.; Verkade, J. G. Org. Lett. 2003, 5, 3787.
32. (a) Cattaway, F. D.; Hoyle, G. J. Chem. Soc. 1923, 654.
33. (b) Buckles, R. E.; Popov, A. I.; Zelezny, W. F.; Smith, R. J. J. Am. Chem. Soc. 1951, 73, 4525.
34. (c) Avramoff, M.; Weiss, J.; Schaechter, O. J. Org. Chem. 1963, 28, 3256.
35. (d) Fisier, L. F.; Fisier, M. Reagents for Organic Synthesis; Wiley: New York, 1967; p 967.
36. (e) Kajigneshi, S.; Kakinami, T.; Tokiyama, H.; Hirakawa, T.; Okamoto, T. Chem. Lett. 1987, 627
37. (f) Muathen, H. A. J. Org. Chem. 1992, 57, 2740.
38. (g) Bora, U.; Bose, G.; Chaudhuri, M. K.; Dhar, S. S.; Gopinath, R.; Khan, A. T.; Patel, B. K. Org. Lett. 2000, 2, 247.
39. (a) Shi, X.; Dai, L. J. Org. Chem. 1993, 58, 4596.
40. (b) Rao, A. V. R.; Singh, A. K.; Reddy, K. M.; Ravikumar, K. J. Chem. Soc., Perkin Trans. 1 1993, 3171.
41. (c) Coats, S. J.; Wasserman, H. H. Tetrahedron Lett. 1995, 36, 7735.
42. (a) Buu-Hoi, N. P. Justus Liebigs Ann. Chem. 1944, 556, 1.
43. (b) Roberts, J. C.; Roffey, P. J. Chem. Soc. (C) 1966, 160.
44. 2/ NaH: Boyd, R. E.; Rasmussen, C. R.; Press, J. B. Synth. Commun. 1995, 25, 1045.
45. 3N: Karimi, S.; Grohmann, K. G. J. Org. Chem. 1995, 60, 554.
46. (e) NBS/NaH: Curran, D. P.; Bosch, E.; Kaplan, J.; Newcomb, M. J. Org. Chem. 1989, 54, 1826.
47. (f) NBS/KH: Curran, D. P.; Chang, C. T. J. Org. Chem. 1989, 54, 3140.
48. (g) NBS/Amberlyst-15: Meshram, H. M.; Reddy, P. N.; Sadashiv, K.; Yadav, J. S. Tetrahedron Lett. 2005, 46, 623.
49. (a) Calo, V.; Ciminale, F.; Lopez, L.; Todesco, P. E. J. Chem. Soc. (C) 1971, 3652.
50. (b) Calo, V.; Ciminale, F.; Lopez, L.; Naso, F.; Todesco, P. E. J. Chem. Soc., Perkin Trans. 1 1972, 2567.
51. (c) Kitahara, Y.; Kato, T.; Ichinose, I. Chem. Lett. 1976, 283.
52. (d) Ichinose, I.; Hosogai, T.; Kato, T. Synthesis 1978, 605 and references therein.
53. (e) Yamaguchi, Y.; Uyehara, T.; Kato, T. Tetrahedron Lett. 1985, 26, 343.
54. (f) Calo, V.; Lopez, L.; Pesce, G.; Todesco, P. E. Tetrahedron 1987, 29, 1625.
55. (g) Tanaka, A.; Oritani, T. Tetrahedron Lett. 1997, 38, 1955.
56. (h) Tanaka, A.; Oritani, T. Tetrahedron Lett. 1997, 38, 7223.
57. (i) Firouzbadi, H.; Iranpoor, N.; Shaterian, H. R. Bull. Chem. Soc. Jpn. 2002, 75, 2195.
58. (j) Toda, F.; Schmeyers, J. Green Chem. 2003, 5, 701.
59. Kavala, V.; Naik, S.; Patel, B. K. J. Org. Chem. 2005, 70, 4267.
60. 3OH. The brominated organic substrate was obtained in satisfactory yield and purity.