Electron transfer induced ring opening of 2-(bromomethyl)aziridines by magnesium in methanol

Tetrahedron

Volumn 58, Issue 35, 2002, Pages 7145-7152

  Tehrani, Kourosch Abbaspour ^a   NguyenVan, Tuyen ^a   Karikomi, Michinori ^a   Rottiers, Mario ^a   De Kimpe, Norbert ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Aziridines

Indexed keywords

1 (4 BROMOBENZYL) 2 BROMOMETHYLAZIRIDINE; 2 BROMOMETHYL 1 (4 METHOXYBENZYL)AZIRIDINE; ALLYLAMINE DERIVATIVE; AZIRIDINE DERIVATIVE; MAGNESIUM; METHANOL; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ELECTRON TRANSPORT; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING;

EID: 0037178973     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(02)00728-7     Document Type: Article

References (38)

1. (a) Li J.J. Tetrahedron. 57:2001;1-24.
2. (b) Beckwith A.L., Ingold K.U. In Rearrangements in the Ground and Excited States. de Mayo, P. Ed.; Academic: New York, 1980
3. (c) Felix N.M., Schlegel H.B., Martin N. J. Org. Chem. 61:1996;8547-8550.
4. (d) Venkat K., Viresh H.R. J. Org. Chem. 62:1997;1572-1573.
5. (e) Daniel J.P. J. Org. Chem. 61:1996;252-256.
6. (f) Derek C.N. Chem. Soc. Rev. 1993;347-359.
7. (g) Martin N., Daryl L.C. J. Am. Chem. Soc. 116:1994;9753-9754.
8. (h) Frederick E.Z., Anders K.P. J. Org. Chem. 60:1995;2666-2667.
9. Dowd P., Zhang W. Chem. Rev. 93:1993;2019-2115.
10. Barton D.H.R., Motherwell R.S.H., Motherwell W.B. J. Chem. Soc., Perkin Trans. 1. 1981;2363-2367.
11. Johns A., Murphy A. Tetrahedron Lett. 29:1988;837-840.
12. (a) Clive D.L.J., Deigneault S. J. Org. Chem. 56:1991;3801-3814.
13. (b) Newcomb M., Glenn A.G. J. Am. Chem. Soc. 111:1989;275-277.
14. (c) Destabel C., Kilburn J.D., Knight J. Tetrahedron. 50:1994;11267-11288.
15. (d) Weng W.W., Luh T.J. J. Org. Chem. 58:1993;5574-5575.
16. (e) Hariharan V., Marc M.G. J. Org. Chem. 60:1995;1053-1059.
17. (a) Dickinson J.M., Murphy J.A. Tetrahedron. 48:1992;1317-1326.
18. (b) Brian A.M., Richard C.T. Tetrahedron Lett. 40:1999;4873-4876.
19. (c) Schwan A.L., Refvik M.D. Tetrahedron Lett. 34:1993;4901-4904.
20. De Smaele D., Bogaert P., De Kimpe N. Tetrahedron Lett. 39:1998;9797-9800.
21. De Kimpe N., Jolie R., De Smaele D. J. Chem. Soc., Chem. Commun. 1994;121-122.
22. De Kimpe N., De Smaele D., Bogaert P. Synlett. 4:1994;287-288.
23. Pak C.S. Korean-Hungarian Collect., Conf. Proc. 1999;69-73.
24. Madabhushi S., Ashok K.B., Narender R. Tetrahedron Lett. 39:1998;2847-2850.
25. Pak C.S., Kim T.H., Ha S.J. J. Org. Chem. 63:1998;10006-10010. and references cited therein.
26. Hutchins R.O., Suchismita Z.R.E., Taffer I.M. Synth. Commun. 19:1989;1519-1522.
27. Lee E., Lee G.H., Pak C.S. J. Org. Chem. 58:1993;1523-1530. and references cited therein.
28. De Kimpe N., De Smaele D., Szakonyi Z. J. Org. Chem. 62:1997;2448-2452.
29. Gensler W.J. J. Am. Chem. Soc. 70:1948;1843-1846.
30. Ali S.I., Nikalje M.D., Sudalai A. Org. Lett. 5:1999;705-707.
31. Kotsuki H., Shimanouchi T., Ohshima R., Fujiwara S. Tetrahedron. 54:1998;2709-2722.
32. Alonso D.A., Andersson P.G. J. Org. Chem. 63:1998;9455-9461.
33. Ginzberg S. Ber. 36:1903;2703-2708.
34. Hayashi K., Sato C., Hiki S., Kumagai T., Tamai S., Abe T., Nagao Y. Tetrahedron Lett. 40:1999;3761-3764.
35. Barluenga J., Canteli R.-M., Flórez J. J. Org. Chem. 59:1994;602-606.
36. Gravestock M.B., Knight D.W., Malik K.M.A., Thornton S.R. J. Chem. Soc., Perkin Trans. 1. 2000;3292-3305.
37. Asensio G., Mello R., Boix-Bernardini C., González-Núñez M.E., Castellano G. J. Org. Chem. 60:1995;3692-3699.
38. Kitagawa O., Suzuki T., Taguchi T. J. Org. Chem. 63:1998;4842-4845.