Vinylic nucleophilic substitution in functionalized 2-vinylpyrroles: a route to a new family of stable enols

Tetrahedron

Volumn 62, Issue 17, 2006, Pages 4146-4152

  Trofimov, Boris A ^a   Petrova, Olga V ^a   Sobenina, Lyubov' N ^a   Drichkov, Vladislav N ^a   Mikhaleva, Al'bina I ^a   Ushakov, Igor' A ^a   Tarasova, Ol'ga A ^a   Kazheva, Olga N ^b   Chekhlov, Anatolii N ^b   Dyachenko, Oleg A ^b  

^a A E FAVORSKY IRKUTSK INSTITUTE OF CHEMISTRY   (Russian Federation)

^b INSTITUTE OF PROBLEMS OF CHEMICAL PHYSICS   (Russian Federation)

Author keywords

2 Vinylpyrroles; 3 Iminopyrrolizines; Vinylic nucleophilic substitution

Indexed keywords

3 IMINOPYRROLIZINE; HYDROXYL GROUP; METHANOL; PYRROLE DERIVATIVE; PYRROLIZINE DERIVATIVE; SODIUM HYDROXIDE; UNCLASSIFIED DRUG; VINYL DERIVATIVE; WATER;

ARTICLE; CHEMICAL BOND; HYDROGEN BOND; ISOMER; MOLECULE; NUCLEAR MAGNETIC RESONANCE; PHOTOCATALYSIS; PHOTODYNAMICS; PRIORITY JOURNAL; SPECTROSCOPY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; X RAY ANALYSIS;

EID: 33646010913     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.02.009     Document Type: Article

References (35)

1. Hayes R.T., Wasielewski M.R., and Gosztola D. J. Am. Chem. Soc. 122 (2000) 5563-5567
2. Harmjanz M., Gill H.S., and Scott M.J. J. Am. Chem. Soc. 122 (2000) 10476-10477
3. Rurach K. Angew. Chem., Int. Ed. 40 (2001) 385-387
4. Wagner R.W., and Lindsey J.S. Pure Appl. Chem. 68 (1996) 1373-1380
5. Burns D.H., and Smith K.M. J. Chem. Res. Miniprint (1990) 1349-1372
6. Murase M., Yoshida S., Hosaka T., and Tobinaga S. Chem. Pharm. Bull. 39 (1991) 489-492
7. Selim M.A. Aswan Sci. Technol. Bull. 13 (1992) 60-72
8. Xiao D., and Ketcha D.M. J. Heterocycl. Chem. 32 (1995) 499-504
9. Trofimov B.A. The Chemistry of Heterocyclic Compounds (1992), Wiley, New York Chapter 2, pp 131-298
10. Sobenina L.N., Demenev A.P., Mikhaleva A.I., and Trofimov B.A. Usp. Khim. 71 (2002) 641-671
11. See also:. Russ. Chem. Rev. 71 (2002) 563-591
12. Trofimov B.A., Sobenina L.N., Demenev A.P., and Mikhaleva A.I. Chem. Rev. 104 (2004) 2481-2506
13. Bakhshi A.K., and Lovleen A. Superlattices Microstruct. 13 (1993) 437-446
14. Berlin A., Canavesi A., Pagani G., Schiavon G., Zecchin S., and Zotti G. Synth. Met. 84 (1997) 451-452
15. Entezami A., and Rahmatpour A. Eur. Polym. J. 34 (1998) 871-878
16. Kim I.T., and Elsenbaumer R.L. Macromolecules 33 (2000) 6407-6411
17. Sour A., Boillot M.-L., Riviere E., and Lesot P. Eur. J. Inorg. Chem. (1999) 2117-2119
18. Sobenina L.N., Mikhaleva A.I., Toryashinova D.-S.D., Kozyreva O.B., and Trofimov B.A. Sulfur Lett. 20 (1996) 9-14
19. Sobenina L.N., Mikhaleva A.I., Toryashinova D.-S.D., Kozyreva O.B., and Trofimov B.A. Sulfur Lett. 20 (1997) 205-212
20. Sobenina L.N., Demenev A.P., Mikhaleva A.I., Petrova O.V., Larina L.I., Chernyhk G.P., Toryashinova D.-S.D., Vashchenko A.V., and Trofimov B.A. Sulfur Lett. 24 (2000) 1-12
21. Sobenina L.N., Demenev A.P., Mikhaleva A.I., Ushakov I.A., Afoninn A.V., Petrova O.V., Elokhina V.N., Volkova K.A., Toryashinova D.-S.D., and Trofimov B.A. Sulfur Lett. 25 (2002) 87-93
22. Schmittel M., Lal M., Schenk W.A., Hagel M., Burzlaff N., and Langels A. Z. Naturforsch. 58b (2003) 877-884
23. O'Neill P., and Hegarty A.F. J. Chem. Soc., Chem. Commun. (1987) 744-745
24. Eberlin A.R., and Williams D.L. J. Chem. Soc., Perkin Trans. 2 (1996) 1043-1046
25. Mukhopadhyaya J.K., Sklenak S., and Rappoport Z. J. Org. Chem. 65 (2000) 6856-6867
26. Mukhopadhyaya J.K., Sklenak S., and Rappoport Z. J. Am. Chem. Soc. 122 (2000) 1325-1336
27. Lei Y.X., Cerioni G., and Rappoport Z. J. Org. Chem. 65 (2000) 4028-4038
28. Nicaise O.J.-C., Mans D.M., Morrow A.D., Hefti E.V., Palkovacs E.M., Singh R.K., Zukowska M.A., and Morin M.D. Tetrahedron 59 (2003) 6433-6443
29. Sobenina L.N., Mikhaleva A.I., Sergeeva M.P., Petrova O.V., Aksamentova T.N., Kozyreva O.B., Toryashinova D.-S.D., and Trofimov B.A. Tetrahedron 51 (1995) 4223-4230
30. Makarov V.A., and Granik V.G. Usp. Khim. 67 (1998) 1013-1031
31. Kalabin G.A., Trofimov B.A., Bzhesovsky V.M., Kushnarev D.F., Amosova S.V., Gusarova N.K., and Al'pert M.L. Izv. AN SSSR (1975) 576-581
32. Wagner G., and Wüthrich K. J. Mol. Biol. 155 (1982) 347-366
33. Bodenhausen G., and Ruben D. J. Chem. Phys. Lett. 69 (1980) 185-189
34. Sheldrick, G. M. SHELXS-9: Program for the refinement of crystal structures, University of Göttingen: Germany, 1997.
35. Verkruijsse H.D., and Brandsma L. J. Organomet. Chem. 332 (1987) 95-98