On the preparation of amine N-oxides by using dioxiranes

Tetrahedron

Volumn 53, Issue 46, 1997, Pages 15877-15888

  Ferrer, Marta ^a   Sánchez Baeza, Francisco ^a   Messeguer, Angel ^a  

^a DEPT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE OXIDE; AROMATIC AMINE; HETEROCYCLIC AMINE; TERTIARY AMINE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; TEMPERATURE;

EID: 2542507637     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10048-5     Document Type: Article

References (38)

1. For reviews on dioxiranes see: a) Curci, R., Dinoi, A., Rubino, M.F. Pure & Appl. Chem. 1995, 67, 811-822.
2. b) Murray, R. W., Chem. Rev. 1989, 89, 1187-1201;
3. Adam, W., Curci, R., Edwards, J.O. Acc. Chem. Res. 1989, 22, 205-211.
4. Gallopo, A.; Edwards, J. J. Org. Chem. 1981, 46, 1684-1688.
5. Templeton, J. F.; Ling, Y.; Zeglam, T. H.; LaBella, F. S. J. Med. Chem. 1993, 36, 42-45.
6. Crandall, J. K.; Reix, T. J. Org. Chem. 1992, 57, 6759-6764.
7. Murray, R. W.; Jeyaraman, R.; Mohan, L. Tetrahedron Lett. 1986, 27, 2335-2336.
8. Murray, R. W.; Rajadhyaksha, S. N.; Mohan, L. J. Org. Chem. 1989, 54, 5783-5788.
9. Murray, R. W.; Singh, M.; Rath, N. Tetrahedron Asymmetry 1996, 7, 1611-1619.
10. Murray, R. W.; Singh, M. Tetrahedron Lett. 1988, 29, 4677-4680.
11. Murray, R. W.; Singh, M. J. Org. Chem. 1990, 55, 2954-2957.
12. Murray, R. W.; Singh, M. Synth. Commun. 1989, 19, 3509-3522.
13. Adam, W.; Briviba, K.; Duschek, F.; Golsch, D.; Kiefer, W.; Sies, H. J. Chem. Soc., Chem. Commun. 1995, 1831-1832.
14. Adam, W.; Golsch, D. Angew. Chem. Int. Ed. Eng. 1993, 105, 771-773.
15. Christian, P. W. N.; Gil, R.; Muñiz-Fernández, K.; Thomas, S. E.; Wierzchleyski, A. T. J. Chem. Soc., Chem. Commun. 1994, 1569-1570.
16. Christian, P. W. N.; Gibson (née Thomas), S. E.; Gil, R.; Jones, P. C. V.; Marcos, C. F.; Prechtl, F.; Wierzchleyski, A. T. Red. Trav. Chim. Pays-Bas 1995, 114, 195-202.
17. Ferrer, M.; Sánchez-Baeza, F.; Messeguer, A.; Diez, A.; Rubiralta, M. J. Chem. Soc., Chem. Commun. 1995, 293-294.
18. Priyadarsini, K. I.; Dennis, M. F.; Naylor, M. A.; Stratford, M. R. L.; Wardman, P. J. Am. Chem. Soc. 1996, 118, 5648-5654.
19. In this case, a second molar equivalent of DMD led to the corresponding epoxy derivative. This result, apparently trivial, was exceptional within all the alkenamines assayed and will be discussed in a forthcoming manuscript.
20. Gibert, M.; Ferrer, M.; Sanchez-Baeza, F.; Messeguer, A. Tetrahedron 1997, 53, 8643-8650.
21. Majumdar, K. C.; Jana, G. H.; Das, U. J. Chem. Soc., Chem. Commun. 1996, 517-518.
22. Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
23. Bischoff, C. A. Chem. Ber. 1901, 34, 2125-2135.
24. Borch, R. F. Tetrahedron Lett. 1968, 61-65.
25. Babayan, A. T.; Martirosyan, G. T. Zhur. Obshchei Khim. 1961, 31, 819-825.
26. Babayan, A. T.; Martirosyan, G. T.; Vartanyan, N. G.; Indzhikkyan, M. G. Zhur. Obshchei Khim. 1960, 30, 2263-2267.
27. Auerbach, M.; Wolffenstein, R. Chem. Ber. 1899, 32, 2507-2521.
28. Chevolot, L.; Husson, A.; Kan-Fan, C.; Husson, H. P.; Potier, P. Bull. Soc. Chim. Fr. 1976, 1222-1226.
29. Sajiki, H. Tetrahedron Lett. 1995, 36, 3465-3468.
30. Bettoni, G.; Franchini, C.; Morlacchi, F.; Tangari, N.; Tortorella, V. J. Org. Chem. 1976, 41, 2780-2782.
31. Hershenson, F. M.; Bauer, L. J. Org. Chem. 1969, 34, 655-660.
32. Balaban, A. T.; Nenitzescu, C. D. J. Chem. Soc. 1961, 3566-3572.
33. Ochiai, E. J. Org. Chem. 1953, 18, 534-551.
34. Cope, A. C.; Lee, H.-H. J. Am. Chem. Soc. 1957, 79, 964-965.
35. Cope, A. C.; Towle, P. H. J. Am. Chem. Soc. 1949, 71, 3423-26.
36. Reynolds, W. F.; Schaefer, T. Can. J. Chem. 1964, 42, 2119-2133.
37. Grammaticakis, T. Comp. Rendus Heb. Sci. 1947, 224, 1568.
38. Davis, M. M.; Hetzer, H. B. J. Am. Chem. Soc. 1954, 76, 4247-4260.