Dioxirane oxidation of substituted vinylphosphonates: A novel efficient route to 1,2-epoxyalkylphosphonates

Journal of Organometallic Chemistry

Volumn 571, Issue 2, 1998, Pages 189-193

  Cristau, Henri Jean ^a   Yangkou Mbianda, Xavier ^a   Geze, Annabelle ^a   Beziat, Yves ^a   Gasc, Marie Bénédicte ^a  

^a Laboratoire de Chimie Macromoleculaire UMR 5076   (France)

Author keywords

1,2 Epoxyphosphonate; Dioxirane; Epoxidation; Oxidation; Vinylphosphonate

Indexed keywords

EID: 0002674504     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(98)00856-0     Document Type: Article

References (37)

1. See for example: H.N. Beck, D.C. Mac Williams, (Dow Chemical Co.); US Pat. 4, 692, 355; Chem. Abs. 107 238808x.
2. See for example: J. Courregelongue, D. Frehel, J.-P. Maffrand, R. Paul, I. Rico, Fr. Pat. 2, 596, 393, Chem. Abs. 108, 94780c.
3. Hendlin D., Stapley E., Jackson M. et al. Sciences. 166:1969;122.
4. Christensen B.G., Leanza W.J., Beattie T.R. et al. Sciences. 166:1969;123.
5. Redmore D. Chem. Rev. 71:1971;315.
6. Sturtz G., Pondaven-Raphalen A. Phosphorus Sulfur. 20:1984;35.
7. N.N. Girotra, N.L. Wendler, Tetrahedron Lett. (1969) 4647.
8. Giordano C., Graziano C. J. Org. Chem. 54:1989;1470.
9. E. Bandini, F. Martinelli, G. Spinta, M. Panunzio, Tetrahedron Assymetry (1995) 2127.
10. G. Sturtz, Bull. Soc. Chim. Fr. (1964) 2333.
11. Kossev K., Troev K., Roundhill D.M. Phosphorus Sulfur Silicon. 83:1993;1.
12. Haake P., Springs B. J. Org. Chem. 41:1976;1165.
13. Inokawa S., Yamamoto M. Phosphorus Sulfur. 16:1983;79.
14. P. Coutrot, P. Savignac, Synthesis (1978) 34.
15. P. Pierrot, J. Villieras, J.F. Normant, Synthesis (1978) 33.
16. Lee K., Shin W.S., Oh D.Y. Synth. Commun. 22:1992;649.
17. Martrinov V.F., Timofeev V.E. Zh. Obsch. Khim. 34:1964;3890.
18. Ulman A., Sprecher M. J. Org. Chem. 44:1979;3703.
19. B.G. Christensen, R.A. Firestone, RA Ger. Offen. (1969) 1,924,135; Chem. Abs. 72 (1970) 43870.
20. B.G. Christensen, R.A. Firestone, RA Ger. Offen. (1969) 1,924,135; Chem. Abs. 72 (1970) 43870.
21. Hunger K. Chem. Ber. 101:1968;3530.
22. G. Sturtz, A. Pondaven-Raphalen, Bull. Soc. Chim. Fr. (1983) 125.
23. E. Ohler, M. El-Baldawi, E. Zbiral, Synthesis (1991) 357.
24. Glamkowski E.J., Gal G., Purick R., Davidson A.J., Sletzinger M. J. Org. Chem. 35:1970;3510.
25. E. Ohler, E. Zbiral, Synthesis (1991) 357.
26. Griffin C.E., Kundu S.K. J. Org. Chem. 34:1969;1532.
27. X. Yangkou Mbianda, Ph. D. Thesis, University of Montpellier II, 1995.
28. H.J. Cristau, M.B. Gasc, X. Yangkou Mbianda, J. Organomet. Chem. 474 (1994) C14.
29. Cristau H.J., Yangkou Mbianda H.X., Beziat Y., Gasc M.B. J. Organomet. Chem. 529:1997;301.
30. Muray R.W. Chem. Rev. 89:1989;1187.
31. Adam W., Curci R., Edwards J.O. Acc. Chem. Res. 22:1989;205.
32. Adam W., Hadjiarapoglou L., Smez A. Chem. Ber. 124:1991;227.
33. R. Curci, M. Fiorentino, M.R. Serio, J. Chem. Soc. Chem. Commun. (1984) 155.
34. Yang D., Wang X-C., Wong M-K., Yip Y-C., Tang M-W. J. Am. Chem. Soc. 118:1996;11311.
35. Wang Z-X., Tu Y., Frohn M., Shi Y. J. Org. Chem. 62:1997;2328.
36. In: Org. Synth., Shinkai vol. 74 (1996) 91.
37. W. Adam, L. Hadjiarapoglou, in: Topics in Current Chemistry, vol. 164, Springer-Verlag, Berlin, 1993, p. 46 and references herein.