Pyridine N-alkylatfon by lithium, magnesium, and zinc alkyl reagents: Synthetic, structural, and mechanistic studies on the bis(imino)pyridine system

Journal of the American Chemical Society

Volumn 127, Issue 16, 2005, Pages 6012-6020

  Blackmore, Ian J ^a   Gibson, Vernon C ^a   Hitchcock, Peter B ^b   Rees, Charles W ^a   Williams, David J ^a   White, Andrew J P ^a  

^a IMPERIAL COLLEGE LONDON   (United Kingdom)

^b UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BINARY MIXTURES; DISSOCIATION; LITHIUM; MAGNESIUM PRINTING PLATES; ORGANIC SOLVENTS; PARAMAGNETIC RESONANCE; PARAMAGNETISM; SPECTROSCOPIC ANALYSIS; THERMODYNAMICS; TOLUENE; ZINC;

CROSSOVER EXPERIMENTS; DEPROTONATION; ELECTRON TRANSFER PROCESS; LIGAND;

ALKYLATION;

LITHIUM; MAGNESIUM; PYRIDINE; SOLVENT; TOLUENE; ZINC;

ALKYLATION; ARTICLE; ATOM; CHEMICAL STRUCTURE; ELECTRON; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; METHYLATION; PROTON TRANSPORT; REACTION ANALYSIS; STRUCTURE ANALYSIS; THERMODYNAMICS;

EID: 17744377764     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja042657g     Document Type: Article

References (37)

1. (a) Small, B. L.; Brookhart, M.; Bennett, A. M. A. J. Am. Chem. Soc. 1998, 120, 4049.
2. (b) Britovsek, G. J. P.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; McTavish, S. J.; Solan, G. A.; White, A. J. P.; Williams, D. J. Chem. Commun. 1998, 849.
3. (c) Britovsek, G. J. P.; Bruce, M.; Gibson, V. C.; Kimberley, B. S.; Maddox, P. J.; Mastroianni, S.; McTavish, S. J. P.; Redshaw, C.; Solan, G. A.; Strömberg, S.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1999, 121, 8728.
4. Reardon, D.; Conan, F.; Gambarotta, S.; Yap, G.; Wang, Q. J. Am. Chem. Soc. 1999, 121, 9318.
5. Estruelas, M. A.; López, A. M.; Méndez, L.; Oliván, M.; Oñate, E. Organometallics 2003, 22, 395.
6. (a) Britovsek, G. J. P.; Mastoianni, S.; Solan, G. A.; Baugh, S. P. D.; Redshaw, C.; Gibson, V. C.; White, A. J. P.; Williams, D. J.; Elsegood, M. R. J. Chem.-Eur. J. 2000, 6, 2221.
7. (b) Ma, Z.; Wang, H.; Qiu, J.; Xu, D.; Hu, Y. Macromol. Rapid Commun. 2001, 22, 1280.
8. (c) Ma, Z.; Sun, W.-H.; Li, Z.-L.; Shao, C.-X.; Hu, Y.-L.; Li, X.-H. Polym. Int. 2002, 51, 994.
9. (d) Britovsek, G. J. P.; Gibson, V. C.; Hoarau, O. D.; Spitzmesser, S. K.; White, A. J. P.; Williams, D. J. Inorg. Chem. 2003, 42, 3454.
10. (e) Chen, Y.; Qian, C.; Sun, J. Organometallics 2003, 22, 1231.
11. (f) Schmidt, R.; Hammon, U.; Gottfried, S.; Welch, M. B.; Alt, H. G. J. Appl. Polym. Sci. 2003, 88, 476.
12. (g) Abu-Surrah, A. S.; Lappalainen, K.; Piironen, U.; Lehmus, P.; Repo, T.; Leskelä, M. J. Organomet. Chem. 2002, 55.
13. (h) Chen, Y.; Chen, R.; Qian, C.; Dong, X.; Sun, J. Organometallics 2003, 22, 4312.
14. (i) Ivanchev, S. S.; Tolstikov, G. A.; Badaev, V. K.; Oleinik, I. I.; Ivancheva, N. I.; Rogozin, D. G.; Oleinki, I. V.; Myakin, S. V. Kinet. Catal. 2004, 45, 176.
15. (j) Paulino, I. S.; Schuchardt, I. J. Mol. Catal. A: Chem. 2004, 211, 55.
16. (k) Bluhm, M. E.; Folli, C.; Döring, M. J. Mol. Catal. A: Chem. 2004, 212, 13.
17. (l) Smit, T. M.; Tomov, A. K.; Gibson, V. C.; White, A. J. P.; Williams, D. J. Inorg. Chem. 2004, 43, 6511.
18. (a) van Koten, G.; Jastrzebski, J. T. B. H.; Vrieze, K. J. Organomet. Chem. 1983, 250, 49.
19. (b) Kaupp, M.; Stoll, H.; Preuss, H.; Kaim, W.; Stahl, T.; van Koten G.; Wissing, E.; Smeets, W. J. J.; Spek, A. L. J. Am. Chem. Soc. 1991, 113, 5606.
20. (c) Kaim, W. Acc. Chem. Res. 1985, 18, 160.
21. (d) Ashby, E. C. Acc. Chem. Res. 1988, 21, 414.
22. (e) Wissing, E.; Kaupp, M.; Boersma, J.; Spek, A. L.; van Koten, G. Organometallics 1994, 13, 2349.
23. Sugiyama, H.; Aharonian, G.; Gambarotta, S.; Yap, G. P. A.; Budzelaar, P. H. M. J. Am. Chem. Soc. 2002, 124, 12268.
24. Reardon, D.; Aharonian, G.; Gambarotta, S.; Yap, G. P. A. Organometallics 2002, 21, 786.
25. Clentsmith, G. K. B.; Gibson, V. C.; Hitchcock, P. B.; Kimberley, B. S.; Rees, C. W. Chem. Commun. 2002, 1498.
26. Khorobkov, I.; Gambarotta, S.; Yap, G. P. A.; Budzelaar, P. H. M. Organometallics 2002, 21, 3088.
27. (a) Bryndza, H. E.; Fong, L. K.; Paciello, R. A.; Tam, W.; Bercaw, J. E. J. Am. Chem. Soc. 1987, 109, 1444.
28. (b) Britovsek, J. G. P.; Cohen, S. A.; Gibson, V. C.; van Meurs, M. J. Am. Chem. Soc. 2004, 126, 10701.
29. (a) Coles, M. P.; Jordan, R. F. J. Am. Chem. Soc. 1997, 119, 8125.
30. (b) Yang, X.; Stern, C. L.; Marks, T. J. J. Am. Chem. Soc. 1994, 116, 10015.
31. For a detailed review, see: Scriven, E. F. V. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Boulton, A. J., McKillop, A., Eds.; Pergamon Press: Oxford, 1984; Vol. 2, p 165.
32. Otwinowski, Z.; Minor, W. In Processing of X-ray Diffraction Data Collected in Oscillation Mode; Carter C. W., Jr., Sweet, R. M., Eds.; Methods in Enzymology, Vol. 276: Macromolecular Crystallography, Part A; Academic Press, 1997; pp 307-326.
33. Blessing, R. H. Acta Crystallogr., Sect. A 1995, 51, 33.
34. Sheldrick, G. M. SHELX97: Programs for Crystal Structure Analysis, release 97-2; Institüt für Anorganische Chemie der Universität: Tammanstrasse 4, D-3400 Göttingen, Germany, 1998.
35. Farrugia, L. J. L. Appl. Crystallogr. 1999, 32, 837.
36. SHELXTL PC, version 5.03; Siemens Analytical X-ray Instruments, Inc.: Madison, WI, 1994. SHELXTL PC, version 5.1; Bruker AXS: Madison, WI, 1997.
37. SHELXTL PC, version 5.03; Siemens Analytical X-ray Instruments, Inc.: Madison, WI, 1994. SHELXTL PC, version 5.1; Bruker AXS: Madison, WI, 1997.