Highly efficient generation of radicals from ester enolates by the ferrocenium ion. application to selective α-oxygenation and dimerization reactions of esters

Journal of Organic Chemistry

Volumn 63, Issue 21, 1998, Pages 7130-7131

  Jahn, Ullrich ^a  

^a TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001004311     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981180m     Document Type: Article

References (32)

1. (a) Tietze, L. F. Chem. Rev. 1996, 96, 115-136.
2. (b) Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131-160.
3. Dalko, P. I. Tetrahedron 1995, 51, 7579-7653.
4. Ghosez, A.; Giese, B.; Zipse, H. In Houben-Weyl - Methoden der Organischen Chemie; 4th ed.; Regitz, M., Giese, ._, Eds.; Thieme: Stuttgart, 1989; Vol. E19a, pp 717-747.
5. (a) Chakraborty, T. K.; Dutta, S. Synth. Commun. 1997, 27, 4163-4172.
6. (b) Braslau, R.; Burrill H, L. C.; Siano, M.; Naik, N.; Howden, R. K.; Mahal, L. K. Macromolecules 1997, 30, 6445-6450 and refs therein.
7. Langer, T.; Illich, M.; Helmchen, G. Synlett 1996, 1137-1139 and refs therein.
8. Quermann, R.; Maletz, R.; Schäfer, H. J. Liebig's Ann. Chem. 1993, 1219-1223 and refs therein.
9. (e) Porter, N. A.; Rosenstein, I. J. Tetrahedron Lett 1993, 34, 7865-7868.
10. (f) Porter, N. A.; Su, Q.; Harp, J. J.; Rosenstein, I. J.; McPhail, A. T. Tetrahedron Lett. 1993, 34, 4457-4460.
11. (g) Rathke, M. W.; Lindert, A. J. Am. Chem. Soc. 1971, 93, 4605-4606.
12. (a) Cohen, T.; McNamara, K.; Kuzemko, M. A.; Ramig, K.; Landi, J. J., Jr.; Dong, Y. Tetrahedron 1993, 49, 7931-7942 and refs therein.
13. (b) Chung, S. K.; Dunn, L. B., Jr. J. Org. Chem. 1983, 48, 1125-1127.
14. Frazier, R. H., Jr.; Harlow, R. L. J. Org. Chem. 1980, 45, 5408-5411.
15. (a) Alvarez-Ibarra, C.; Csaky, A. G.; Colmenero, B.; Quiroga, M. L. J. Org. Chem. 1997, 62, 2478-2482 and refs therein.
16. (b) Brocksom, T. J.; Petragnani, N.; Rodrigues, R.; La Scala Texeira, H. Synthesis 1975, 396-397.
17. (a) Schmittel, M. Top. Curr. Chem. 1994, 169, 183-230.
18. (b) Schäfer, H. J. Angew. Chem., Int. Ed. Engl. 1981, 20, 911-933.
19. Tokuda, M.; Shigei, T.; Itoh, M. Chem. Lett. 1975, 621-624.
20. Jahn, U.; Hartmann, P. Chem. Commun. 1998, 209-210.
21. 4b
22. For configuration assignment see ref 4d.
23. 8 was probably formed during enolate generation.
24. For configuration assignment see: (a) Sakai, T.; Nakamura, T.; Fukuda, K.; Amano, E.; Utaka, M.; Takeda, A. Bull. Chem. Soc. Jpn. 1986, 59, 3185-3188.
25. (b) Shing, T. K. M.; Tarn, E. K. W.; Tai, V. W.-F.; Chung, I. H. F.; Jiang, Q. Chem. Eur. J. 1996, 2, 50-57.
26. Frater, G. Helv. Chim. Acta 1979, 62, 2825-2832.
27. Davis, F. A.; Chen, B.-C. In Houben-Weyl - Methods of Organic Chemistry; 4th ed.; Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Thieme: Stuttgart, 1995; Vol. E21e, pp 4497-4518.
28. Boger, D. L.; Garbaccio, R. M.; Jin, Q. J. Org. Chem. 1997, 62, 8875-8891.
29. For configuration assignment see: Irie, H.; Kitagawa, T.; Miyashita, M.; Zhang, Y. Chem. Pharm. Bull. 1991, 39, 2545-2549.
30. Hawker, C. J. Acc. Chem. Res. 1997, 30, 373-382.
31. Heathcock, C. H. In Modern Synthetic Methods; Scheffold, R., Ed.; Verlag Helvetica Chimica Acta: Basel, 1992; Vol. 6, pp 1-102.
32. 4e,f