7Li residual quadrupolar couplings as a powerful tool to identify the degree of organolithium aggregation

Angewandte Chemie - International Edition

Volumn 51, Issue 31, 2012, Pages 7843-7846

  Pöppler, Ann Christin ^a   Keil, Helena ^a   Stalke, Dietmar ^a   John, Michael ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

aggregation; alignment media; lithium; NMR spectroscopy; quadrupolar nuclei

Indexed keywords

AGGREGATION STATE; HEXAMERS; LI-NMR SPECTRUM; LITHIUM AMIDE; LOW TEMPERATURES; ORGANOLITHIUMS; ORGANOMETALLIC COMPOUNDS; QUADRUPOLAR COUPLING; QUADRUPOLAR NUCLEUS; SPECTROSCOPIC PROPERTY; TETRAMERS;

AGGLOMERATION; AMIDES; COUPLINGS; DIMERS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANOMETALLICS; POLYSTYRENES;

LITHIUM;

LITHIUM; ORGANOMETALLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY;

LITHIUM; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS;

EID: 84864398729     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201202116     Document Type: Article

References (59)

1. "Organoalkali Chemistry":, M. Schlosser, in Organometallics in Synthesis. A Manual (Ed.:, M. Schlosser,), Wiley, New York, 2002
2. J. Clayden, Organolithiums: Selectivity for Synthesis, Elsevier, Pergamon, Oxford, 2002
3. D. M. Hodgson, in Organolithiums in Enantioselective Synthesis, Vol. 5, Springer, Berlin, 2003.
4. T. Stey, D. Stalke, The Chemistry of Organolithium Compounds (Eds.:, Z. Rappoport, I. Marek,), Wiley, Chichester, 2004, pp. 47-120
5. V. H. Gessner, C. Däschlein, C. Strohmann, Chem. Eur. J. 2009, 15, 3320-3334.
6. P. A. Scherr, R. J. Hogan, J. P. Oliver, J. Am. Chem. Soc. 1974, 96, 6055-6059
7. M. Bühl, N. J. R. v. E. Hommes, P. v. R. Schleyer, U. Fleischer, W. Kutzelnigg, J. Am. Chem. Soc. 1991, 113, 2459-2465.
8. D. Seebach, R. Hässig, J. Gabriel, Helv. Chim. Acta 1983, 66, 308-337
9. K. Sorger, W. Bauer, P. v. R. Schleyer, D. Stalke, Angew. Chem. 1995, 107, 1766-1768
10. Angew. Chem. Int. Ed. Engl. 1995, 34, 1594-1596
11. H. J. Reich, D. P. Green, M. A. Medina, W. S. Goldenberg, B. Ö. Gudmundsson, R. R. Dykstra, N. H. Philips, J. Am. Chem. Soc. 1998, 120, 7201-7210.
12. K. F. Morris, C. S. Johnson, Jr., J. Am. Chem. Soc. 1992, 114, 3141-3142.
13. K. W. Henderson, D. S. Walther, P. G. Williard, J. Am. Chem. Soc. 1995, 117, 8680-8681
14. I. Keresztes, P. G. Williard, J. Am. Chem. Soc. 2000, 122, 10228-10229.
15. W. Bauer, P. v. R. Schleyer, Magn. Reson. Chem. 1988, 26, 827-833.
16. M. Granitzka, A.-C. Pöppler, E. K. Schwarze, D. Stern, T. Schulz, M. John, R. Herbst-Irmer, S. K. Pandey, D. Stalke, J. Am. Chem. Soc. 2012, 134, 1344-1351.
17. R. M. Gschwind, Angew. Chem. 2005, 117, 4744-4746
18. Angew. Chem. Int. Ed. 2005, 44, 4666-4668
19. C. M. Thiele, Eur. J. Org. Chem. 2008, 5673-5685
20. G. Kummerlöwe, B. Luy, Annu. Rep. NMR Spectrosc. 2009, 68, 193-232
21. G. Kummerlöwe, B. Luy, TrAC Trends Anal. Chem. 2009, 28, 483-493.
22. G. Kummerlöwe, S. L. Grage, C. M. Thiele, I. Kuprov, A. S. Ulrich, B. Luy, J. Magn. Reson. 2011, 209, 19-30
23. F. Hallwass, M. Schmidt, H. Sun, A. Mazur, G. Kummerlöwe, B. Luy, A. Navarro-Vázquez, C. Griesinger, U. M. Reinscheid, Angew. Chem. 2011, 123, 9659-9662
24. Angew. Chem. Int. Ed. 2011, 50, 9487-9490.
25. C. Canlet, D. Merlet, P. Lesot, A. Meddour, A. Loewenstein, J. Courtieu, Tetrahedron: Asymmetry 2000, 11, 1911-1918
26. P. Lesot, C. Aroulanda, NMR Spectroscopy of Liquid Crystals (Ed.:, R. Y. Dong,), World Scientific, Singapore, 2010.
27. A. Meddour, I. Canet, A. Loewenstein, J. M. Péchiné, J. Courtieu, J. Am. Chem. Soc. 1994, 116, 9652-9656
28. C. M. Thiele, S. Berger, Org. Lett. 2003, 5, 705-708.
29. B. Deloche, E. T. Samulski, Macromolecules 1981, 14, 575-581
30. B. Luy, K. Kobzar, H. Kessler, Angew. Chem. 2004, 116, 1112-1115
31. Angew. Chem. Int. Ed. 2004, 43, 1092-1094.
32. B. Böttcher, V. Schmidts, J. A. Raskatov, C. M. Thiele, Angew. Chem. 2010, 122, 210-214
33. Angew. Chem. Int. Ed. 2010, 49, 205-209.
34. F. Fujiwara, L. W. Reeves, A. S. Tracey, J. Am. Chem. Soc. 1974, 96, 5250-5251
35. G. Lindblom, H. Wennerström, B. Lindman, J. Magn. Reson. 1976, 23, 177
36. J. Borgström, P.-O. Quist, L. A. Piculell, Macromolecules 1996, 29, 5926-5933
37. P. W. Kuchel, B. E. Chapman, N. Müller, W. A. Bubb, D. J. Philp, A. M. Torres, J. Magn. Reson. 2006, 180, 256-265.
38. P. P. Man in Encyclopedia of Magnetic Resonance (Eds.: R. K. Harris, R. E. Wasylishen), Wiley, Chichester, 2011, DOI:.
39. D. Merlet, J. Emsley, P. Lesot, J. Courtieu, J. Chem. Phys. 1999, 111, 6890-6896.
40. B. Luy, K. Kobzar, S. Knör, J. Furrer, D. Heckmann, H. Kessler, J. Am. Chem. Soc. 2005, 127, 6459-6465.
41. G. H. Miller, A. F. Perizzolo, J. Polym. Sci. 1955, 18, 411-416.
42. U. Wannagat, H. Niederprüm, Chem. Ber. 1961, 94, 1540-1547
43. D. B. Collum, Acc. Chem. Res. 1993, 26, 227-234.
44. D. E. Woessner, Concepts Magn. Reson. 2001, 13, 294-325.
45. G. Kummerlöwe, E. F. McCord, S. F. Cheatham, S. Niss, R. W. Schnell, B. Luy, Chem. Eur. J. 2010, 16, 7087-7089.
46. B. L. Lucht, D. B. Collum, J. Am. Chem. Soc. 1994, 116, 6009-6010
47. S. Popenova, R. c. Mawhinney, G. Schreckenbach, Inorg. Chem. 2007, 46, 3856-3864.
48. P. Stanetty, M. D. Mihovilovic, J. Org. Chem. 1997, 62, 1514-1515.
49. C. Strohmann, V. H. Gessner, Angew. Chem. 2007, 119, 4650-4653
50. Angew. Chem. Int. Ed. 2007, 46, 4566-4569.
51. M. A. Nichols, P. G. Williard, J. Am. Chem. Soc. 1993, 115, 1568-1572
52. N. D. R. Barnett, R. E. Mulvey, W. Clegg, P. A. O'Neil, J. Am. Chem. Soc. 1993, 115, 1573-1574.
53. T. Kottke, D. Stalke, Angew. Chem. 1993, 105, 619-621
54. Angew. Chem. Int. Ed. Engl. 1993, 32, 580-582.
55. J. G. Snijders, C. A. de Lange, E. E. Burnell, J. Chem. Phys. 1983, 79, 2964-2969
56. C. A. de Lange, W. L. Meerts, A. C. J. Weber, E. E. Burnell, J. Phys. Chem. A 2010, 114, 5878-5887.
57. D. Johnels, H. Günther, The Chemistry of Organolithium Compounds (Eds.:, Z. Rappoport, I. Marek,), Wiley, Chichester, 2004, pp. 137-203.
58. L. M. Jackman, L. M. Scarmoutzos, C. W. DeBrosse, J. Am. Chem. Soc. 1987, 109, 5355-5361.
59. J. W. Zwanziger, M. Torrent, Appl. Magn. Reson. 2008, 33, 447-456.