Electrochemically induced hetero-[4+2]-cycloaddition reactions between 2-vinylpyrroles and β-acceptor-substituted enamines

Chemistry - A European Journal

Volumn 4, Issue 1, 1998, Pages 107-112

  Peglow, Thomas ^a   Blechert, Siegfried ^a   Steckhan, Eberhard ^b  

^a TECHNISCHE UNIVERSITÄT BERLIN   (Germany)

^b UNIVERSITY OF BONN   (Germany)

Author keywords

Cations; Cycloadditions; Electrochemistry; Electron transfer; Radical ions

Indexed keywords

EID: 0031887130     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(sici)1521-3765(199801)4:1<107::aid-chem107>3.0.co;2-e     Document Type: Article

References (33)

1. a) C. F. Gürtler, E. Steckhan, S. Blechert, Synlett 1994, 141;
2. b) C. F. Gürtler, E. Steckhan, S. Blechert, Angew. Chem. 1995, 107, 2025; Angew. Chem. Int. Ed. Engl. 1995, 34, 1901;
3. b) C. F. Gürtler, E. Steckhan, S. Blechert, Angew. Chem. 1995, 107, 2025; Angew. Chem. Int. Ed. Engl. 1995, 34, 1901;
4. c) C. F. Gürtler, E. Steckhan, S. Blechert, J. Org. Chem. 1996, 61, 4136.
5. For a review see: a) N. L. Bauld, Tetrahedron 1989, 45, 5307; b) N. L. Bauld, D. J. Bellville, B. Harirchian, K. T. Lorenz, R. A. Pabon, D. W. Reynolds, D. D. Wirth, H. Chiou, B. K. Marsh. Acc. Chem. Res. 1987, 20,371; c) H. Chanon, L. Eberson in Photoinduced Electron Transfer Reactions (Eds.: M. A. Fox, M. Chanon), Elsevier, Amsterdam, 1988, p. 409.
6. For a review see: a) N. L. Bauld, Tetrahedron 1989, 45, 5307; b) N. L. Bauld, D. J. Bellville, B. Harirchian, K. T. Lorenz, R. A. Pabon, D. W. Reynolds, D. D. Wirth, H. Chiou, B. K. Marsh. Acc. Chem. Res. 1987, 20,371; c) H. Chanon, L. Eberson in Photoinduced Electron Transfer Reactions (Eds.: M. A. Fox, M. Chanon), Elsevier, Amsterdam, 1988, p. 409.
7. For a review see: a) N. L. Bauld, Tetrahedron 1989, 45, 5307; b) N. L. Bauld, D. J. Bellville, B. Harirchian, K. T. Lorenz, R. A. Pabon, D. W. Reynolds, D. D. Wirth, H. Chiou, B. K. Marsh. Acc. Chem. Res. 1987, 20,371; c) H. Chanon, L. Eberson in Photoinduced Electron Transfer Reactions (Eds.: M. A. Fox, M. Chanon), Elsevier, Amsterdam, 1988, p. 409.
8. a) G. O. Schenk, S. P. Mannsfield, G. Schomburg, C. H. Krauch, Z. Naturforsch. 1964, B19, 18;
9. b) R. Schutte, G. R. Freeman, J. Am. Chem. Soc. 1969, 91, 3715;
10. c) G. S. Hammond, T. L. Penner, D. G. Whitten, ibid. 1970, 92, 2861.
11. a) D. W. Raynolds, N. L. Bauld, Tetrahedron 1986, 42, 6189;
12. b) P. G. Gassmann, D. A. Singleton, J. Am. Chem. Soc. 1984, 106, 7993.
13. J. Mlcoch, E. Steckhan, Tetrahedron Lett. 1987, 28, 1081.
14. B. Harirchian, N. L. Bauld, J. Am. Chem. Soc. 1989, 111, 1826.
15. a) A. Gieseler, E. Steckhan, O. Wiest, F. Knoch, J. Org. Chem. 1991, 56.1405;
16. b) O. Wiest, E. Steckhan, F. Grein, ibid. 1992, 57, 4034;
17. c) O. Wiest, E. Steckhan, Tetrahedron Lett. 1993, 34, 6391.
18. O. Wiest, E. Steckhan, Angew. Chem. 1993, 105, 932; Angew. Chem. Int. Ed. Engl. 1993, 32, 901.
19. O. Wiest, E. Steckhan, Angew. Chem. 1993, 105, 932; Angew. Chem. Int. Ed. Engl. 1993, 32, 901.
20. T. Wirth, S. Blechert, Tetrahedron Lett. 1992, 33, 6621.
21. a) P. G. Pickup, R. A. Osteryoung, J. Am. Chem. Soc. 1984, 106, 2294;
22. b) G. Tourillon, F. Garnier, J. Electroanal. 1982, 135, 173.
23. E. Winterfeldt, H. Preuss, Chem. Ber. 1966, 99, 450.
24. D. V. Gardner, D. E. McGreer, Can. J. Chem. 1970, 48, 2104.
25. a) H. H. Wasserman, J. L. Ives. J. Org. Chem 1978, 43, 3228;
26. b) H. Bredereck, F. Effenberger, T. Brendle, H. Muffler, Chem. Ber. 1968, 101, 1885.
27. E. Wenkert, K. G. Dave, F. Haglid, R. G. Lewis, T. Oishi, R. V. Stevens, M. Terashima. J. Org. Chem. 1968, 33, 747.
28. Ring opening is achieved by refluxing in methanolic hydrochloric acid. See: S. Takano, T. Sato, K. Inomato, K. Ogasawara J. Chem. Soc. Chem. Commun. 1991, 462.
29. O. Diels, K. Alder, Justus Liebigs Ann. Chem. 1932, 498, 1.
30. A. Treibs, R. Zinsmeister, Chem. Ber. 1957, 90, 87.
31. A. J. Saggiomo, J. Org. Chem. 1957, 22, 1171.
32. A. Treibs, R. Schmidt, R. Zinsmeister, Chem. Ber. 1957, 90, 79.
33. H. Berner, G. Schulz, H. Reinshagen, Monatsh. Chem. 1977, 108, 915.