Novel reactions of β-oxidophosphonium ylides with perhaloalkanes - A facile route to trisubstituted halo olefins

Acta Chimica Sinica

Volumn 59, Issue 9, 2001, Pages 1507-1512

  Zhang, Xiong Zhi ^a   Hu, Jin Shan ^a   Li, Xing Ya ^a   Fu, Wei Min ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

oxidophosphonium ylides; Halophilic attack; Perhaloalkanes; Trisubstituted halo olefins

Indexed keywords

EID: 0042872377     PISSN: 05677351     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. Li, X.-Y; Jiang, X.-K; Pan, H.-Q; Hu, J.-S; Fu, W.-M. Pure & Appl. Chem., 1987, 59, 1015.
2. Li, X.-Y; Hu, J.-S. Tetrahedron Lett., 1987, 28, 6317.
3. (a) Marfat, A.; McGuirk, P. R.; Kramer, R.; Helquist, P. J. Am. Chem. Soc., 1977, 99, 253.
4. (b) Corey, E. J.; Katzenellenbogen, J. A. J. Am. Chem. Soc., 1969, 91, 1851.
5. (c) Roush, W. R.; Riva, R. J. Org. Chem., 1988, 53, 710.
6. Johnson, W. S. Acc. Chem. Res., 1968, 1, 1.
7. (a) Trost, B. M. Acc. Chem. Res., 1970, 3, 120.
8. (b) Sidall, J. B. In Chemical Ecology, Ed. by Sondherimer, E.; Simeone, J. B., Academic Press, New York, 1970, p.282.
9. Gardette, M.; Jabri, N.; Alexakis, A.; Normant, J. F. Tetrahedron, 1984, 40, 2741.
10. (a) Zembayashi, M.; Tamao, K.; Kumada, M. Synthesis, 1977, 422.
11. (b) Julia, M.; Blasioli, C. Bull. Soc. Chim. Fr., 1976, 1941.
12. (c) Elitti-Bianchi, G.; Centini, F.; Re, L. J. Org. Chem., 1976, 41, 1648.
13. (d) Hart, D. W.; Blackburn, T. F.; Schwartz, J. J. Am. Chem. Soc., 1975, 97, 679.
14. (a) Camps, F.; Coll, J.; Llebaria, A.; Moreto, J. M. Tetrahedron Lett., 1988, 29, 5811.
15. (b) Paquette, L. A.; Dahnke, K.; Doyon, J.; He, W.; Wyant, K.; Friedrich, D. J. Org. Chem., 1991, 56, 6199.
16. (c) Sharma, S.; Oehlschlager, A. O. J. Org. Chem., 1989, 54, 5064.
17. (d) Bestmann, H. J.; Arenz, T. Tetrahedron Lett., 1986, 27, 1995.
18. (e) Miller, J. A. J. Org. Chem., 1989, 54, 998.
19. (f) Khadija, M.; Bouchra, M.; Ariz, A.; Helene, M.; Christian, R. Tetrahedron Lett., 1999, 40, 59.
20. (g) Huang, Z.-Z.; Wu, L. L.; Zhu, L. S.; Huang, X. Synth. Commun., 1996, 26, 677.
21. (h) Huang, Z.-Z.; Lan, G.-C.; Huang, X. Synth. Commun., 1998, 28, 633.
22. (a) Schlosser, M.; Christmann, K. F. Angew. Chem. Int. Ed. Engl., 1966, 5, 126.
23. (b) Schlosser, M.; Christmann, K. F. Ann. Chem., 1967, 708, 1.
24. (a) Schlosser, M.; Christmann, K.-F. Synthesis, 1969, 38.
25. (b) Corey, E. J.; Shulman, J. I.; Yamamoto, H. Tetrahedron Lett., 1970, 447.
26. Pross, A.; Sternhell, S. Aust. J. Chem., 1971, 24, 1437.
27. (a) Wittig, G.; Wittenberg, D. Ann., 1957, 606, 1.
28. (b) House, H. O.; Rasmisson, G. H. J. Org. Chem., 1961, 26, 4278.
29. Okuhara, K. J. Org. Chem., 1978, 43, 2745.
30. (a) Cousseau, J.; Gouin, L. J. Chem. Soc. Perkin Trans. 1, 1977, 1797.
31. (b) Fahey, R. C.; Schubert, C. J. Am. Chem. Soc., 1965, 87, 5172.
32. Millon, J.; Lorne, R.; Linstrumelle, G. Synthesis, 1975, 434.
33. Pross, A.; Sternhell, S. Aust. J. Chem., 1970, 23, 989.
34. Davis, D. R.; Roberts, J. D. J. Am. Chem. Soc., 1962, 84, 2252.