Electrophilic activation of hydrogen peroxide: Selective oxidation reactions in perfluorinated alcohol solvents

Organic Letters

Volumn 2, Issue 18, 2000, Pages 2861-2863

  Neimann, Karine ^a   Neumann, Ronny ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000253554     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006287m     Document Type: Article

References (17)

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7. (a) Bartlett, P. D.; Leffler, J. E. J. Am. Chem. Soc. 1950, 72, 3030.
8. (b) Chong, A. O.; Sharpless, K. B. J. Org. Chem. 1977, 42, 1587.
9. There are recent reports of trifluoroethanol as a "magic" solvent for catalytic epoxidation reactions, (a) van Viliet, M. C. A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 821.
10. (b) van Viliet, M. C. A.; Arends, I. W. C. E.; Sheldon, R. A. Chem. Commun. 1999, 263.
11. (c) Shryne, T. M.; Kim, L. US Patent 4024165, 1977.
12. Reactions were carried out in 5 mL vials by mixing the organic substrate, hydrogen peroxide, and solvent in the quantities given in the tables. The vials were magnetically stirred at ambient temperature, ∼22 °C, or in a thermostated bath at 60 °C. The mixtures were analyzed by GC (HP 5890) and GC-MS (HP 5973) using a 30 m 5% phenyl methyl silicone column (ID 0.32 mm, coating 0.25 μm).
13. Formation of perfluoroacetone could lead to subsequent formation of the α-hydroxy hydroperoxides and epoxidation of alkenes. cf. Ganesh-pure, P. A.; Adam, W. Synthesis 1996, 179.
14. Ravikumar, K. S.; Begue, J. P.; Bonnet-Delpon, D. Tetrahedron Lett. 1998, 39, 3141.
15. (b) Ravikumar, K. S.; Zhang, Y. M.; Begue, J. P.; Bonnet-Delpon, D. Eur. J. Org. Chem. 1998, 2937.
16. 2O without locking.
17. 17O shifts assigned to the hydroxyl oxygen are at 40.5 ppm for 2-propanol and at - 11.7 ppm for HFIP.