Carbodiimide-promoted Epoxidation of Olefins with Dilute Aqueous Hydrogen Peroxide

Synlett

Volumn 1996, Issue 7, 1996, Pages 649-651

  Majetich, George ^a   Hicks, Rodgers ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000873018     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-5574     Document Type: Article

References (14)

1. a) Payne, G. B. Tetrahedron 1962, 18, 763.
2. b) Venturello, C.; Abneri, M.; Ricci, M. J. Org. Chem. 1983, 48, 3831.
3. c) Reynaud, J. P.; Battioni, P.; Bartoli, J. F.; Mansuy, D. J. Chem. Soc. Chem. Commun. 1985, 888.
4. d) Rebek, J.; McCready, R. Tetrahedron Lett. 1979, 1001, 4337.
5. e) Heggs, R. P.; Ganem, B. J. Am. Chem. Soc. 1979, 101, 2484.
6. f) Chen, Y.; Reymond, J.-L. Tetrahedron Lett. 1995, 36, 4015.
7. 4, is more reactive in displacement reactions because of the α-effect. See: McIsaac, J. E.; Subbaraman, L. R.; Subbaraman, J.; Mulhausen, H. A.; Behrman, E. J. J. Org. Chem. 1972, 37, 1037.
8. 2 with DCC and either acidic or basic catalysts does not result in epoxidation.
9. 2 with DCC and either acidic or basic catalysts does not result in epoxidation.
10. a) Spectroscopic data obtained for all new compounds were fully consistent with the assigned structures. b) All yields are isolated yields. c) Reaction conditions have not been fully optimized.
11. When EDC was used an extra equivalent of base was added to replace that consumed by the ammonium salt.
12. 2; and 24 → 48 hours at 25°C. f) 1 equiv. of olefin; 1.3 equiv. of mCPBA; 1 → 12 hours at 25°C.
13. Williams, A.; Brahim, I. T. Chem. Rev. 1981, 81, 589-636.
14. Desai, M. C.; Stramiello, L. M.S. Tetrahedron Lett. 1993, 34, 7685.