1,2- Vs 1,4-Regioselectivity of Lithiated Phenylacetonitrile toward α,βUnsaturated Carbonyl Compounds. 2. Relation between the Regioselectivity and the Structure of the Species in Solution

Journal of Organic Chemistry

Volumn 63, Issue 10, 1998, Pages 3295-3301

  Strzalko, Tekla ^a   Seyden Penne, Jacqueline ^a   Wartski, Lya ^a   Corset, Jacques ^b   Castella Ventura, Martine ^b   Froment, Françoise ^b  

^a CNRS   (France)

^b UNIVERSITÉ DES SCIENCES ET TECHNOLOGIES DE LILLE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001234617     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9715175     Document Type: Article

References (24)

1. (a) Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds; Pergamon Press: London, 1991; Vol. 4.
2. (b) Arseniyadis, S.; Kyler, K. S.; Watt, D. S. Org. React. 1984, 31, 1-364.
3. (a) Croizat, D.; Seyden-Penne, J.; Strzalko, T.; Wartski, L.; Corset, J.; Froment, F. J. Org. Chem. 1992, 57, 6435.
4. (b) Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Froment, F.; Corset, J. Tetrahedron Lett. 1994, 35, 3935.
5. (c) Sauvêtre, R.; Roux-Schmitt, M. C.; Seyden-Penne, J. Tetrahedron 1978, 34, 2135.
6. (d) Roux, M. C.; Wartski, L.; Seyden-Penne, J. Tetrahedron 1981, 37, 1927.
7. (e) Hatzigrigoriou, E.; Wartski, L.; Seyden-Penne, J.; Toromanoff, E. Tetrahedron 1985, 41, 5045.
8. (a) Stork, G.; Ozorio, A. A.; Leong, A. Y. W. Tetrahedron 1978, 5175.
9. (b) Roux, M. C. Seuron, N.; Seyden-Penne, J. Synthesis 1983, 494.
10. Hunig, S.; Wehner, G. Chem. Ber. 1980, 113, 302.
11. Deschamps, B. Tetrahedron 1978, 34, 2009.
12. (a) Zervos, M.; Wartski, L.; Seyden-Penne, J. Tetrahedron 1986, 42, 4963.
13. (b) Enders, D.; Kirchoff, J.; Mannes, D.; Raabe, G. Synthesis 1995, 659.
14. (c) Roux, M. C.; Wartski, L.; Nierlich, M.; Lance, M. Tetrahedron 1994, 50, 8445.
15. Strzalko, T.; Seyden-Penne, J.; Wartski, L.; Corset, J.; Castella-Ventura, M.; Froment, F. J. Org. Chem. 1998, 63, 3287-3294.
16. (a) Chabanel, M.; Paoli, D. J. Chim. Phys. 1980, 77, 913.
17. (b) Chabanel, M. Pure Appt. Chem. 1990, 62, 35.
18. Morin, P. G.; Solum, M. S.; Withers, J. D.; Grant, D. M. J. Magn. Reson. 1982, 48, 138.
19. El-Bouz, M.; Wartaki, L.; Seyden-Penne, J. J. Organomet. Chem. 1979, 177, 17.
20. Carlier, P. R.; Lo, K. M. J. Org. Chem. 1994, 59, 4053.
21. Carlier, P. R.; Lo, K. M.; Williams, I. D. J. Org. Chem. 1995, 60, 7511.
22. Kaufmann, E.; Schleyer, P. v. R.; Houk, K. N.; Wu, Y. D. J. Am. Chem. Soc. 1985, 107, 5560.
23. Baron, M. H.; Jaeschke, H.; Moravie, R. M.; De Loze, C.; Corset, J. Metal-ligand interactions in organic chemistry and biochemistry; Pullmann, B., Goldblum, N., Eds.; Reidel D. Publishing Co: Dordrecht, Holland, 1977, Part 1, p 171.
24. Nakamura, M.; Nakamura, E.; Koga, N.; Morokuma, K. J. Am. Chem. Soc. 1993, 115, 11016.