Solution and solid-state characteristics of imine adducts with tris(pentafluorophenyl)borane

Organometallics

Volumn 21, Issue 7, 2002, Pages 1400-1407

  Blackwell, James M ^a   Piers, Warren E ^a   Parvez, Masood ^a   McDonald, Robert ^b  

^a UNIVERSITY OF CALGARY   (Canada)

^b UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; HYDROGENATION; ISOMERIZATION; LIGHT POLARIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION KINETICS; SINGLE CRYSTALS; STACKING FAULTS; SYNTHESIS (CHEMICAL); THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

SOLID STATE STRUCTURES;

ORGANOMETALLICS;

EID: 0000420605     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om011086n     Document Type: Article

References (47)

1. Larock, R. C. Comprehensive Organic Transformations, 2nd ed.; Wiley-VCH: New York, 1999; pp 835-866.
2. (a) Denmark, S. E.; Nicaise, O. J.-C. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: New York, 1999; Vol. 2, pp 923-964.
3. (b) Bloch, R. Chem. Rev. 1998, 98, 1407.
4. (c) Enders, D.; Reinhold, U. Tetrahedron: Asymmetry 1997, 8, 1895.
5. Aubreoht, K. B.; Winemillar, M. D.; Collum, D. B. J. Am. Chem. Soc. 2000, 122, 11084.
6. (a) Keck, G. E.; Enholdm, E. J. J. Org. Chem. 1985, 50, 146.
7. (b) Shimizu, M.; Kume, K.; Fujisawa, T. Tetrahedron Lett, 1982, 23, 3739.
8. (c) Chen, C.-M.; Brown, H. C. J. Am. Chem. Soc. 2000, 122, 4217.
9. Willoughby, C. A.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 8952.
10. Of course, many examples of transition-metal and main-group complexes that incorporate ligands in which an imine function is part of a chelate array exist; we do not include this class of compounds in this statement.
11. (a) Parks, D. J.; Piers, W. E. J. Am. Chem. Soc. 1996, 118, 9440.
12. (b) Parks, D. J.; Blackwell, J. M.; Piers, W. E. J. Org. Chem. 2000, 65, 3090.
13. (c) Blackwell, J. M.; Piers, W. E. Org. Lett. 2000, 2, 695.
14. (d) Blackwell, J. M.; Piers, W. E.; McDonald, R. J. Am. Chem. Soc. 2002, 124, 1295.
15. Blackwell, J. M.; Sonmor, E.; Scoccitti, T.; Piers, W. E. Org. Lett. 2000, 2, 3921.
16. (a) Massey, A. G.; Park, A. J.; Stone, F. G. A. Proc. Chem. Soc. 1963, 212.
17. (b) Massey, A. G.; Park, A. J. J. Organomet. Chem. 1964, 2, 245.
18. For reviews on the use of this Lewis acid in organic synthesis see: (a) Piers, W. E.; Chivers, T. Chem. Soc. Rev. 1997, 345.
19. (b) Ishihara, K.; Yamamoto, Eur. J. Org. Chem. 1999, 527, 7. For a review on its use in organometallic chemistry see: Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
20. (b) Ishihara, K.; Yamamoto, Eur. J. Org. Chem. 1999, 527, 7. For a review on its use in organometallic chemistry see: Chen, E. Y.-X.; Marks, T. J. Chem. Rev. 2000, 100, 1391.
21. 3 as a Lewis acid in organic transformations: (a) Blackwell, J. M.; Foster, K. L.; Beck, V. H.; Piers, W. E. J. Org. Chem, 1999, 64, 4887.
22. (b) Hassfield, J.; Christmann, M.; Kalesse, M. Org. Lett. 2001, 3, 3561.
23. (c) Gevorgyan, V.; Liu, J.-X.; Rubin, M.; Benson, S.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 8919.
24. (d) Gevorgyan, V.; Rubin, M.; Benson, S.; Liu, J.-X.; Yamamoto, Y. J. Org. Chem. 2000, 65, 6179.
25. (e) Rubin, M.; Gevorgyan, V. Org. Lett. 2001, 3, 2705.
26. (f) Imamura, K.; Yoshikawa, E.; Gevorgyan, V.; Sudo, T.; Asao, N.; Yamamoto, Y. Can. J. Chem. 2001, 79, 1624.
27. (a) Röttger, D.; Erker, G.; Fröhlich, R.; Kotila, S. J. Organomet. Chem. 1996, 518, 17.
28. (b) Bradley, D. C.; Hursthouse, M. B.; Motevalli, M.; Zheng, D. H. J. Chem. Soc., Chem. Commun. 1991, 7.
29. (c) Bradley, D. C.; Harding, I. S.; Keefe, A. D.; Motevalli, M.; Zheng, D. H. J. Chem. Soc., Dalton Trans. 1996, 3931.
30. (d) Parks, D. J.; Piers, W. E.; Parvez, M.; Atencio, R.; Zaworotko, M. J. Organometallics 1998, 17, 1369.
31. Acid-catalyzed isomerizations of imines generally occur only in the presence of a nucleophile (usually the counteranion of the acid moiety): Johnson, J. E.; Morales, N. M.; Gorczyca, A. M.; Dolliver, D. D.; McAllister, M. A. J. Org. Chem. 2001, 66, 7979 and references therein.
32. McCarty, C. G. In The Chemistry of the Carbon-Nitrogen Double Bond; Patai, S., Ed.; Wiley-Interscience: Toronto, 1970; p 363.
33. Döring, S.; Erker, G.; Fröhlich, R.; Meyer, O.; Bergander, K. Organometallics 1998, 17, 2183.
34. Jacobsen, H.; Berke, H.; Döring, S.; Kehr, G.; Erker, G.; Fröhlich, R.; Meyer, O. Organometallics 1999, 18, 1724.
35. Williams, J. H. Acc. Chem. Res. 1993, 26, 593.
36. Cozzi, F.; Ponzini, F.; Annunziata, R.; Cinquinei, M.; Siegel, J. S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1019.
37. (a) Coates, G. W.; Waymouth, E. M. Science 1995, 267, 217.
38. (b) Pietsch, M. A.; Rappe, A. K. J. Am. Chem. Soc. 1996, 118, 10908.
39. (c) Coates, G. W.; Dunn, A. R.; Henling, L. M.; Dougherty, D. A.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1997, 36, 248.
40. (d) Coates, G. W.; Dunn, A. R.; Henling, L. M.; Ziller, J. W.; Lobkovsky, E. B.; Grubbs, R. H. J. Am. Chem. Soc. 1998, 120, 3641.
41. (e) Weck, M.; Dunn, A. R.; Matsumoto, K.; Coates, G. W.; Lobkovsky, E. B.; Grubbs, R. H. Angew. Chem., Int. Ed. 1999, 38, 2741.
42. (f) Dai, C.; Nguyen, P.; Marder, T. B.; Scott, A. J.; Clegg, W.; Viney, C. Chem. Commun. 1999, 2493.
43. teXan: Crystal Structure Analysis Package; Molecular Structure Corp., 1985, 1992.
44. Sheldrick, G. M., SHELXTL97: Program for Crystal Structure Determination; University of Göttingen, Göttingen, Germany, 1997.
45. Programs for diffractometer operation, data collection, data reduction, and absorption correction were those supplied by Bruker.
46. Sheldrick, G. M. Acta Crystallogr. 1990, A46, 467-473.
47. Sheldrick, G. M. SHELXL-93: Program for Crystal Structure Determination; University of Göttingen, Göttingen, Germany, 1993.