Theoretical Study of the Reaction of Alkyllithium with Pyridylphosphines

Journal of Organic Chemistry

Volumn 63, Issue 4, 1998, Pages 1131-1137

  Budzelaar, Peter H M ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000258455     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9716136     Document Type: Article

References (36)

1. G. R. Newkome Chem. Rev. (Washington, D.C.) 1993, 93, 2067.
2. Drent, E. Eur. Pat. Appl. EP.-A-271144, 1988. Drent, E.; Budzelaar, P. H. M.; Jager, W. W. Eur. Pat. Appl. EP.-A-386833, 1990. Drent, E.; Budzelaar, P. H. M.; Jager W. W.; Stapersma, J. Eur. Pat. Appl. EP.-A-441447, 1991. Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1993, 455, 247 and 1994, 475, 57; see also ref 4.
3. Drent, E. Eur. Pat. Appl. EP.-A-271144, 1988. Drent, E.; Budzelaar, P. H. M.; Jager, W. W. Eur. Pat. Appl. EP.-A-386833, 1990. Drent, E.; Budzelaar, P. H. M.; Jager W. W.; Stapersma, J. Eur. Pat. Appl. EP.-A-441447, 1991. Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1993, 455, 247 and 1994, 475, 57; see also ref 4.
4. Drent, E. Eur. Pat. Appl. EP.-A-271144, 1988. Drent, E.; Budzelaar, P. H. M.; Jager, W. W. Eur. Pat. Appl. EP.-A-386833, 1990. Drent, E.; Budzelaar, P. H. M.; Jager W. W.; Stapersma, J. Eur. Pat. Appl. EP.-A-441447, 1991. Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1993, 455, 247 and 1994, 475, 57; see also ref 4.
5. Drent, E. Eur. Pat. Appl. EP.-A-271144, 1988. Drent, E.; Budzelaar, P. H. M.; Jager, W. W. Eur. Pat. Appl. EP.-A-386833, 1990. Drent, E.; Budzelaar, P. H. M.; Jager W. W.; Stapersma, J. Eur. Pat. Appl. EP.-A-441447, 1991. Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1993, 455, 247 and 1994, 475, 57; see also ref 4.
6. Drent, E. Eur. Pat. Appl. EP.-A-271144, 1988. Drent, E.; Budzelaar, P. H. M.; Jager, W. W. Eur. Pat. Appl. EP.-A-386833, 1990. Drent, E.; Budzelaar, P. H. M.; Jager W. W.; Stapersma, J. Eur. Pat. Appl. EP.-A-441447, 1991. Drent, E.; Arnoldy, P.; Budzelaar, P. H. M. J. Organomet. Chem. 1993, 455, 247 and 1994, 475, 57; see also ref 4.
7. Budzelaar, P. H. M.; Frijns, J. H. G.; Orpen, A. G. Organometallics 1990, 9, 1222. Fennis, P. J.; Budzelaar, P. H. M.; Frijns, J. H. G.; Orpen, A. G. J. Organomet. Chem. 1990, 393, 287.
8. Budzelaar, P. H. M.; Frijns, J. H. G.; Orpen, A. G. Organometallics 1990, 9, 1222. Fennis, P. J.; Budzelaar, P. H. M.; Frijns, J. H. G.; Orpen, A. G. J. Organomet. Chem. 1990, 393, 287.
9. Drent, E.; Budzelaar, P. H. M. Eur. Pat. Appl EP.-A-386834, 1990.
10. Kyba, E. P.; Hudson, C. W. Tetrahedron Lett. 1975, 1869. Kyba, E. P. J. Am. Chem. Soc. 1975, 97, 2554 and 1976, 98, 4805.
11. Kyba, E. P.; Hudson, C. W. Tetrahedron Lett. 1975, 1869. Kyba, E. P. J. Am. Chem. Soc. 1975, 97, 2554 and 1976, 98, 4805.
12. Kyba, E. P.; Hudson, C. W. Tetrahedron Lett. 1975, 1869. Kyba, E. P. J. Am. Chem. Soc. 1975, 97, 2554 and 1976, 98, 4805.
13. Scriven, E. F. V. Pyridines and their Benzo Derivatives: Reactivity at ring carbon atoms. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon: New York, 1984; Vol 2, p 262ff.
14. Lyle, R. E. Partially Reduced Pyridines. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Supplement part I; Wiley: New York, 1974; p 156; see also ref 6.
15. Uchida, Y.; Kawai, M.; Masauji, H.; Oae, S. Heteroatom Chem. 1993, 4, 421.
16. Ogawa, S.; Sato, S.; Furukawa, N. Tetrahedron Lett. 1992, 33, 7925.
17. Furukawa, N.; Tsuruoka, M.; Fujihara, H. Heterocycles 1986, 24, 3337.
18. Uenishi, J.; Tanaka, T.; Wakabayashi, S.; Oae, S.; Tsukube, H. Tetrahedron Lett. 1990, 31, 4625.
19. Uchida, Y.; Kozawa, H.; Oae, S. Tetrahedron Lett. 1989, 30, 6365.
20. Uchida, Y.; Onoue, K.; Tada, N.; Nagao, F.; Oae, S. Tetrahedron Lett. 1989, 30, 567; Newkome, G.; Hager, D. C. J. Am. Chem. Soc. 1978, 100, 5567.
21. Uchida, Y.; Onoue, K.; Tada, N.; Nagao, F.; Oae, S. Tetrahedron Lett. 1989, 30, 567; Newkome, G.; Hager, D. C. J. Am. Chem. Soc. 1978, 100, 5567.
22. Oae, S.; Uchida, Y. Ace. Chem. Res. 1991, 24, 202.
23. GAMESS.-UK V5.2. GAMESS.-UK is a package of ab initio programs written by Guest, M. F.; Van Lenthe, J. H.; Kendrick, J.; Schoffel, K.; Sherwood, P.; Harrison, R. J., with contributions from Amos, R. D.; Buenker, R. J.; Dupuis, M.; Handy, N. C.; Hillier, I. H.; Knowles, P. J.; Bonacic-Koutecky, V.; Von Niessen, W.; Saunders: V. R.; Stone. A. J. The package is derived from the original GAMESS code due to Dupuis, M.; Spangler D.; Wendoloski, J.; NRCC Software Catalog, Vol. 1, Program No. QG01 (GAMESS), 1980. MP2 implementation: Rice, J. E.; Amos, R. D.; Handy, N. C.; Lee T. J.; Schaefer, H. F. J. Chem. Phys. 1986, 85, 963. Watts, J. D.; Dupuis, M. J. Comput. Chem. 1988, 9, 158.
24. GAMESS.-UK V5.2. GAMESS.-UK is a package of ab initio programs written by Guest, M. F.; Van Lenthe, J. H.; Kendrick, J.; Schoffel, K.; Sherwood, P.; Harrison, R. J., with contributions from Amos, R. D.; Buenker, R. J.; Dupuis, M.; Handy, N. C.; Hillier, I. H.; Knowles, P. J.; Bonacic-Koutecky, V.; Von Niessen, W.; Saunders: V. R.; Stone. A. J. The package is derived from the original GAMESS code due to Dupuis, M.; Spangler D.; Wendoloski, J.; NRCC Software Catalog, Vol. 1, Program No. QG01 (GAMESS), 1980. MP2 implementation: Rice, J. E.; Amos, R. D.; Handy, N. C.; Lee T. J.; Schaefer, H. F. J. Chem. Phys. 1986, 85, 963. Watts, J. D.; Dupuis, M. J. Comput. Chem. 1988, 9, 158.
25. GAMESS.-UK V5.2. GAMESS.-UK is a package of ab initio programs written by Guest, M. F.; Van Lenthe, J. H.; Kendrick, J.; Schoffel, K.; Sherwood, P.; Harrison, R. J., with contributions from Amos, R. D.; Buenker, R. J.; Dupuis, M.; Handy, N. C.; Hillier, I. H.; Knowles, P. J.; Bonacic-Koutecky, V.; Von Niessen, W.; Saunders: V. R.; Stone. A. J. The package is derived from the original GAMESS code due to Dupuis, M.; Spangler D.; Wendoloski, J.; NRCC Software Catalog, Vol. 1, Program No. QG01 (GAMESS), 1980. MP2 implementation: Rice, J. E.; Amos, R. D.; Handy, N. C.; Lee T. J.; Schaefer, H. F. J. Chem. Phys. 1986, 85, 963. Watts, J. D.; Dupuis, M. J. Comput. Chem. 1988, 9, 158.
26. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939. Gordon, M. S.; Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1982, 104, 2797. Pietro, W. J.; Francl, M. M.; Hehre, W. J.; DeFrees, D. J.; Pople J. A.; Binkley, J. S. J. Am. Chem. Soc. 1982, 104, 5039.
27. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939. Gordon, M. S.; Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1982, 104, 2797. Pietro, W. J.; Francl, M. M.; Hehre, W. J.; DeFrees, D. J.; Pople J. A.; Binkley, J. S. J. Am. Chem. Soc. 1982, 104, 5039.
28. Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1980, 102, 939. Gordon, M. S.; Binkley, J. S.; Pople, J. A.; Hehre, W. J. J. Am. Chem. Soc. 1982, 104, 2797. Pietro, W. J.; Francl, M. M.; Hehre, W. J.; DeFrees, D. J.; Pople J. A.; Binkley, J. S. J. Am. Chem. Soc. 1982, 104, 5039.
29. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Bmkley, J. S.; Gordon, M. S.; DeFrees D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 66, 217.
30. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Bmkley, J. S.; Gordon, M. S.; DeFrees D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 66, 217.
31. Hehre, W. J.; Ditchfield, R.; Pople, J. A. J. Chem. Phys. 1972, 56, 2257. Francl, M. M.; Pietro, W. J.; Hehre, W. J.; Bmkley, J. S.; Gordon, M. S.; DeFrees D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654. Hariharan, P. C.; Pople, J. A. Chem. Phys. Lett. 1972, 66, 217.
32. Spek, A. L. The EUCLID package. In Computational Crystallography; Sayre, D., Ed.; Clarendon Press: Oxford, 1982.
33. Steiner, A.; Stalke, D. J. Chem. Soc., Chem. Commun. 1993, 444. Steiner, A.; Stalke, D. Organometallics 1995, 14, 2422.
34. Steiner, A.; Stalke, D. J. Chem. Soc., Chem. Commun. 1993, 444. Steiner, A.; Stalke, D. Organometallics 1995, 14, 2422.
35. Marsden, C. J.; Smart, B. A. Organometallics 1995, 14, 5399.
36. Stone, A. J. Chem. Phys. Lett. 1983, 83, 233.