Oxidation of secondary alcohols with phenyltrimethylammonium tribromide in the presence of a catalytic amount of antimony(III) bromide or copper(II) bromide

Synlett

Volumn , Issue 13, 2004, Pages 2369-2373

  Sayama, Shinsei ^a   Onami, Tetsuo ^a  

^a FUKUSHIMA MEDICAL UNIVERSITY   (Japan)

Author keywords

Alcohol; Antimony(III) bromide; Copper(II) bromide; Oxidation; Phenyltrimethylammonium tribromide

Indexed keywords

1,2 DIOL; ALCOHOL; ANTIMONY BROMIDE; ANTIMONY DERIVATIVE; COPPER BROMIDE; COPPER DERIVATIVE; GLYCOL; HYDROBENZOIN; KETOL; KETONE DERIVATIVE; PHENYLTRIMETHYLAMMONIUM; PHENYLTRIMETHYLAMMONIUM TRIBROMIDE; STRONTIUM; UNCLASSIFIED DRUG;

ALCOHOL OXIDATION; ARTICLE; CATALYSIS; CHEMICAL BOND; REACTION ANALYSIS; ROOM TEMPERATURE; SYNTHESIS;

EID: 8744270356     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-832840     Document Type: Article

References (43)

1. Larock, R. C. In Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999, 1234.
2. Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 1523.
3. Kakiuchi, N.; Maeda, Y.; Nishimura, T.; Uemura, S. J. Org. Chem. 2001, 66, 6620.
4. Man, Z.; Shinokubo, H.; Oshima, K. Synlett 2001, 1421.
5. Friedrich, H. B.; Khan, F.; Singh, N.; Staden, M. Synlett 2001, 869.
6. Mukaiyama, T.; Matsuo, J.; Iida, D.; Kitagawa, H. Chem. Lett. 2001, 846.
7. Martin, S. E.; Suares, D. F. Tetrahedron Lett. 2002, 43, 4475.
8. Ghorbani-Vaghei, R.; Khazaei, A. Tetrahedron Lett. 2003, 44, 7525.
9. Takahashi, M.; Oshima, K.; Matsubara, S. Tetrahedron Lett. 2003, 44, 9201.
10. (a) Saigo, K.; Morikawa, A.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1976, 49, 1656.
11. (b) Ueno, Y.; Okawara, M. Tetrahedron Lett. 1976, 4597.
12. (c) David, S.; Thieffry, A. J. Chem. Soc., Perkin Trans, 1 1979, 1568.
13. (a) Akiba, K.-y.; Shimizu, A.; Ohnari, H.; Ohkata, K. Tetrahedron Lett. 1985, 26, 3211.
14. (b) Akiba, K.-y.; Shimizu, A.; Ohnari, H.; Ohkata, K. Chem. Lett. 1985, 1577.
15. (c) Huang, Y.; Shen, Y.; Chen, C. Synthesis 1985, 651.
16. Ho, T.-L. In Fiesers' Reagents for Organic Synthesis, Vol. 1-21; John Wiley and Sons; New York, 1967-2003.
17. Sayama, S.; Inamura, Y. Bull. Chem. Soc. Jpn. 1991, 64, 306.
18. Sayama, S.; Inamura, Y. Chem. Lett. 1996, 633.
19. Yamamoto, J.; Ito, S.; Tsuboi, T.; Tsuboi, T.; Tsukihara, K. Bull. Chem. Soc. Jpn. 1985, 58, 470.
20. Ishihara, K. In Lewis Acids in Organic Synthesis, Vol. 2; Yamamoto, H., Ed.; Wiley-VCH; New York, 2000, 523.
21. (a) Corey, E. J.; Palani, A. Tetrahedron Lett, 1995, 36, 7945.
22. (b) Karthikeyan, G.; Perumal, P. T. Synlett 2003, 2249.
23. Nakano, T.; Terada, T.; Ishii, Y.; Ogawa, M. Synthesis 1986, 774.
24. Bovicelli, P.; Lupattelli, P.; Sanetti, A.; Mincione, E. Tetrahedron Lett. 1994, 35, 8477.
25. Frigerio, M.; Santagostino, M. Tetrahedron Lett. 1994, 35, 8019.
26. Bovicelli, P.; Lupattelli, P.; Sanetti, A.; Mincione, E. Tetrahedron Lett. 1995, 36, 3031.
27. Iwahama, T.; Sakaguchi, S.; Nishiyama, Y.; Ishii, Y. Tetrahedron Lett. 1995, 36, 6923.
28. Linares, M. L.; Sanchez, N.; Alajarin, R.; Vaquero, J. J.; Alvarez-Builla, J. Synthesis 2001, 382.
29. Yamaguchi, J.; Takeda, T. Chem. Lett. 1992, 423.
30. Ferguson, G.; Ajjou, A. N. Tetrahedron Lett. 2003, 44, 9139.
31. 2-pyridine at r.t.
32. Tomioka, H.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1982, 23, 539.
33. Stevens, R. V.; Chapman, K. T.; Stubbs, C. A.; Tam, W. W.; Albizati, K. F. Tetrahedron Lett. 1982, 23, 4647.
34. Kaneda, K.; Kawanishi, Y.; Jitsukawa, K.; Teranishi, S. Tetrahedron Lett. 1983, 24, 5009.
35. Masuyama, Y.; Takahashi, M.; Kurusu, Y. Tetrahedron Lett. 1984, 25, 4417.
36. Kim, K. S.; Chung, S.; Cho, I. H.; Hahn, C. S. Tetrahedron Lett. 1989, 30, 2559.
37. Choudary, B. M.; Durgaprasad, A.; Valli, V. L. K. Tetrahedron Lett. 1990, 31, 5785.
38. Paul, A. M.; Khandekar, A. C.; Shenoy, M. A. Synth. Commun. 2003, 33, 2581.
39. Sharma, V. B.; Jain, S. L.; Sain, B. Tetrahedron Lett. 2003, 44, 383.
40. Martin, S. E.; Garrone, A. Tetrahedron Lett, 2003, 44, 549.
41. Mandelic acid methylester and ethyl 3-hydroxybutyrate were recovered unchanged in 92-95% yields atr.t. for 17-18 h. 1,4-Dichloro-2-butanol was also recovered unchanged in 90% yield at r.t, for 17 h.
42. Benzyl alcohol was recovered in 60-75% yields for 17-24 h. Benzaldehyde dimethylacetal was gradually afforded in 13-32% yields for 48-72 h.
43. 3 (3:1 v/v). Benzil (3, 50 mg, 0.24 mmol) was obtained in 96% yield.