Bismuth(III) oxide perchlorate promoted rearrangement of epoxides to aldehydes and ketones

Tetrahedron Letters

Volumn 41, Issue 10, 2000, Pages 1527-1530

  Anderson, Andrew M ^a   Blazek, Jesse M ^a   Garg, Parie ^a   Payne, Brian J ^a   Mohan, Ram S ^a  

^a ILLINOIS WESLEYAN UNIVERSITY   (United States)

Author keywords

Bismuth; Bismuth compounds; Epoxides; Rearrangements

Indexed keywords

ALDEHYDE DERIVATIVE; BISMUTH DERIVATIVE; EPOXIDE; KETONE DERIVATIVE; PERCHLORATE;

ARTICLE; CATALYST; CHEMICAL REACTION; CONTROLLED STUDY; ECOTOXICITY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034603555     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02330-8     Document Type: Article

References (19)

1. (a) Gorzynski Smith, J. Synthesis 1984, 8, 629.
2. (b) Parker, R. E.; Issacs, N. S. Chem Rev. 1959, 59, 737.
3. © Rao, A. S.; Paknikar, S. K.; Kirtane, J. G. Tetrahedron 1983, 39, 2323.
4. (a) House, H. O. J. Am. Chem. Soc. 1955, 70, 3070.
5. (b) Rickborn, B.; Gerkin, R. M. J. Am. Chem. Soc. 1971, 93, 1693.
6. © Kulasegaram, S.; Kulawiec, R. J. J. Org. Chem. 1997, 62, 6547.
7. (d) Ranu, B. C.; Jana, U. J. Org. Chem. 1998, 63, 8212.
8. Garrett R. L. In Designing Safer Chemicals; ACS Symposium Series 640; American Chemical Society: Washington, DC, 1996; Chapter 1.
9. (a) Reglinski, J. In Chemistry of Arsenic, Antimony and Bismuth; Norman, N. C., Ed.; Blackie Academic and Professional: New York, 1998; pp. 403-440.
10. (b) Marshall, J. A. Chemtracts 1997, 1064-1075.
11. © Suzuki, H.; Ikegami, T.; Matano, Y. Synthesis. 1997, 249.
12. Garrigues, B.; Gonzanga, F.; Robert, H.; Dubac, J. J. Org. Chem. 1997, 62, 4880
13. Wada, M.; Takegichi, E.; Matsumoto, T. Bull. Chem. Soc. Jpn. 1991, 64, 990.
14. Ohki, H.; Wada, M.; Akiba, K. Tetrahedron Lett. 1988, 29, 4719.
15. 2O was purchased from Aldrich Chemical Company and used as received. While we did not encounter any problems with this reagent, caution should be exercised in handling perchlorates.
16. Barry, C. N.; Evans, S. A. J. Org. Chem. 1983, 48, 2825.
17. Lewis, J. B.; Hedrick, G. W. J. Org. Chem. 1965, 30, 4271.
18. Gensler, W. J.; Koehler, W. R. J. Org. Chem. 1962, 27, 2754.
19. Halterman, R. T.; McEnvoy, M. A. J. Am. Chem. Soc. 1990, 112, 6690