Epoxide Formation by Indirect Electroreductive Coupling between Aldehydes or Ketones and Activated gem-Dichloro Compounds

Synthesis

Volumn , Issue 3, 2004, Pages 389-400

  Oudeyer, S ^a   Leonel E ^a   Paugam, J P ^a   Nedelec J Y ^a  

^a CNRS Université Paris Est Créteil Val de Marne   (France)

Author keywords

Aldehydes; Condensation; Coupling; Epoxides; Ketones; Reductions

Indexed keywords

ALDEHYDES; CHLORINE COMPOUNDS; KETONES; PEROXIDES;

ELECTROREDUCTIVE COUPLING; EPOXIDES;

CHEMICAL REACTIONS;

ALDEHYDE DERIVATIVE; CHLORINE DERIVATIVE; EPOXIDE; KETONE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; ELECTROLYSIS; POLYMERIZATION; REACTION ANALYSIS;

EID: 1442286433     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-815915     Document Type: Article

References (46)

1. Sengmany, S.; Léonel, E.; Paugam, J. P.; Nédélec, J.-Y. Synthesis 2002, 533.
2. Oudeyer, S.; Léonel, E.; Paugam, J. P.; Nédélec, J.-Y. Tetrahedron 2003, 59, 1073.
3. Lynch, B. M.; Pausacker, K. H. J. Chem. Soc. 1955, 1525.
4. Gupta, K. C.; Nigam, R. K.; Srivastava, N. Indian Curr. Sci. 1984, 53, 191.
5. (a) Heck, R. F. Org. React. 1982, 27, 345.
6. (b) Sho, C. S.; Uemura, S. J. Organomet. Chem. 1994, 465, 85.
7. Bellucci, G.; Chiappe, C.; Cordoni, A. Tetrahedron: Asymmetry 1996, 7, 197.
8. (a) Lane, J. F.; Walters, D. R. J. Am. Chem. Soc. 1951, 73, 4234.
9. (b) Shaap, A. P.; Siddiqui, S.; Prasad, G.; Palomino, E.; Sandison, M. Tetrahedron 1985, 41, 2229.
10. (c) Simmamura, O.; Suzuki, H. Bull. Chem. Soc. Jpn. 1954, 27, 231.
11. Cope, A. C.; Trumbull, P. A.; Trumbull, E. R. J. Am. Chem. Soc. 1958, 80, 2844.
12. (a) Tiffeneau, M.; Levy, J. Bull. Soc. Chim. Fr. 1931, 49, 1806.
13. (b) Kayser, F. Ann. Chim. Paris 1936, 6, 144.
14. (c) Ogata, Y.; Tabushi, I. J. Am. Chem. Soc. 1961, 83, 3440.
15. (d) Lazzeretti, P.; Taddei, F.; Torre, G. Org. Magn. Resonance 1973, 5, 385.
16. Frohn, M.; Wang, Z. X.; Shi, Y. J. Org. Chem. 1998, 63, 6425.
17. Zadok, E.; Amar, D.; Mazur, Y. J. Am. Chem. Soc. 1980, 102, 6370.
18. Nishino, H.; Satoh, H.; Yamashita, M.; Kurosawa, K. J. Chem. Soc., Perkin Trans. 2 1999, 1919.
19. Comprehensive Organic Transformation, A Guide to Functional Group Preparation; Larock, R. C., Ed.; VCH: New York, 1989, 457.
20. Yamada, T.; Takai, T.; Rhode, O.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1991, 64, 2109.
21. Cainelli, G.; Tangari, N.; Umani Ronchi, A. Tetrahedron 1972, 28, 3009.
22. Kessar, S. V.; Singh, P.; Kaur, N. P.; Chawla, U.; Shulka, K.; Aggarwal, P.; Venugopal, D. J. Org. Chem. 1991, 56, 3908.
23. Delmond, B.; Pommier, J. C.; Valade, J. J. Organomet. Chem. 1972, 35, 91.
24. Tamura, Y.; Bayomi, S. M.; Sumoto, K.; Ikeda, M. Synthesis 1977, 693.
25. Johnson, C. R.; Mori, K.; Nakanishi, A. J. Org. Chem. 1979, 44, 2065.
26. (a) Corey, E. J.; Chaykovsky, M. J. Am. Chem. Soc. 1962, 84, 867.
27. (b) Corey, E. J.; Oppolzer, W. J. Am. Chem. Soc. 1964, 86, 1899.
28. Hatch, M. J. J. Org. Chem. 1969, 34, 2133.
29. (a) Aggarwal, V. K.; Abdel-Rahman, H.; Fan, L.; Jones, R. V. H.; Standen, M. C. H. Chem.-Eur. J. 1996, 8, 1024.
30. (b) Aggarwal, V. K.; Alonso, E.; Hynd, G.; Lyndon, K. M.; Palmer, M. J.; Porcelloni, M.; Studley, J. R. Angew. Chem. Int. Ed. 2001, 40, 1430.
31. Padwa, A.; Gasdaska, J. R. Tetrahedron 1988, 44, 4147.
32. Zhong, K.; Shao, J.; Liu, C.; Lu, R. Synth. Commun. 1991, 21, 869.
33. Shanklin, J. R.; Johnson, C. R.; Ollinger, J.; Coates, R. M. J. Am. Chem. Soc. 1973, 95, 3429.
34. Durandetti, M.; Périchon, J.; Nédélec, J.-Y. Tetrahedron Lett. 1999, 40, 9009.
35. Léonel, E.; Paugam, J. P.; Heintz, M.; Nédélec, J.-Y. Synth. Commun. 1999, 29, 4015.
36. Conan, A.; Sibille, S.; Périchon, J. J. Org. Chem. 1991, 56, 2018.
37. Fleisher, R.; Galle, D.; Braun, M. Liebigs Ann. Recl. 1997, 1189.
38. Inoue, Y.; Yamasaki, N.; Shimoyama, H.; Tai, A. J. Org. Chem. 1993, 58, 1785.
39. Murray, R. W.; Singh, M.; Jeyaraman, R. J. Am. Chem. Soc. 1992, 114, 1346.
40. Bulman Page, P. C.; Rassias, G. A.; Bethell, D.; Schilling, M. B. J. Org. Chem. 1998, 63, 2774.
41. Dansette, P. M.; Ziffer, H.; Jerina, D. M. Tetrahedron 1976, 32, 2071.
42. Zanardi, J.; Leriverend, C.; Aubert, D.; Julienne, K.; Metzer, P. J. Org. Chem. 2001, 66, 5620.
43. Fetizon, M.; Henry, Y.; Aranda, G.; Audier, H. E.; DeLuzes, H. Org. Mass. Spectrom. 1974, 8, 201.
44. Majima, T.; Tojo, S.; Ishida, A.; Takamuku, S. J. Org. Chem. 1996, 61, 7793.
45. Solladié-Cavallo, A.; Diep-Vohuule, A.; Sunjic, V.; Vinkovic, V. Tetrahedron: Asymmetry 1996, 7, 1783.
46. Solladié-Cavallo, A.; Lupattelli, P.; Marsol, C.; Isarno, T.; Bonini, C.; Caruso, L.; Maiorella, A. Eur. J. Org. Chem. 2002, 1439.