Modification of the Swern oxidation: Use of stoichiometric amounts of an easily separable, recyclable, and odorless sulfoxide that can be polymer-bound

Journal of Organic Chemistry

Volumn 61, Issue 22, 1996, Pages 7856-7859

  Liu, Yaoquan ^a   Vederas, John C ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000435633     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961438d     Document Type: Article

References (16)

1. For reviews see: (a) Tidwell, T. T. Synthesis 1990, 857-870. (b) Tidwell, T. T. Org. React. 1990, 39, 297-572. (c) Mancuso, A. J.; Swern, D. Synthesis 1981, 165-185.
2. For reviews see: (a) Tidwell, T. T. Synthesis 1990, 857-870. (b) Tidwell, T. T. Org. React. 1990, 39, 297-572. (c) Mancuso, A. J.; Swern, D. Synthesis 1981, 165-185.
3. For reviews see: (a) Tidwell, T. T. Synthesis 1990, 857-870. (b) Tidwell, T. T. Org. React. 1990, 39, 297-572. (c) Mancuso, A. J.; Swern, D. Synthesis 1981, 165-185.
4. (a) Mancuso, A. J.; Huang, S.-L.; Swern, D. J. Org. Chem. 1978, 43, 2480-2482.
5. (b) Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651-1660.
6. (c) Mancuso, A. J.; Brownfain, D. S.; Swern, D. J. Org. Chem. 1979, 44, 4148-4150.
7. In 100 g quantities, 6-bromohexanoic acid is typically five times more expensive than dimethyl sulfoxide.
8. Clements, A. P.; White, R. H.; Ferry, J. G. Arch. Microbiol. 1993, 159, 296-300.
9. (a) Leonard, N. J.; Johnson, C. R. J. Org. Chem. 1962, 27, 282-284.
10. (b) Johnson, C. R.; Keiser, J. E. Organic Syntheses; Wiley: New York, 1973; Coll. Vol. 5, pp 791-793.
11. Methanethiol has a bp 5.95°C at 760 mm and the lethal concentration in air for rats is 10,000 ppm: Merck Index, 11th ed.; Merck: Rahway, NJ, 1983; No. 5867, p 5862.
12. Methyl ester 7 is readily available by a number of routes including diazomethane esterification of 1. It can also be used effectively in the Swern reaction.
13. Marx, M.; Tidwell, T. T. J. Org. Chem. 1984, 49, 788-793.
14. Crosby, G. A.; Weinshenker, N. M.; Uh, H.-S. J. Am. Chem. Soc. 1975, 97, 2232-2235.
15. Witter, D. J.; Vederas, J. C. J. Org. Chem. 1996, 61, 2613-2623.
16. Purification of Laboratory Chemicals, 3rd ed.; Perrin, D. D., Armarego, W. L. F., Eds.; Pergamon: New York, 1988.