Structurally stimulated deprotonation/alumination of the TMP anion

Angewandte Chemie - International Edition

Volumn 49, Issue 18, 2010, Pages 3182-3184

  Conway, Ben ^a   Kennedy, Alan R ^a   Mulvey, Robert E ^a   Robertson, Stuart D ^a   Álvarez, Joaquin García ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

Author keywords

Alkali metals; Aluminum; Amides; Metalation steric effects

Indexed keywords

METALATIONS; STERIC EFFECT;

ALUMINUM; AMIDES; POTASSIUM;

THERMOMECHANICAL PULPING PROCESS;

EID: 77951614490     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201000181     Document Type: Article

References (44)

1. a) C. L. Kissel. B. Rickborn, J. Org. Chem. 1972, 37, 2060;
2. b) M. W. Rathke, R. Kow, J. Am. Chem. Soc. 1972, 94, 6854;
3. c) R. A. Olofson, C. M. Dougherty, J. Am. Chem. Soc 1973, 95, 581;
4. d) R. A. Olofson, C. M. Dougherty, J. Am. Chem. Soc. 1973, 95, 582.
5. M. Campbell, V. Snieckus in Encyclopedia of Reagents for Organic Synthesis. Vol.5 (Ed.: L. A. Paquette), Wiley, Chichester, 1995.
6. a) N. D. R. Barnett, R. E. Mulvey, W. Clegg, P. A. O'Neil, J. Am. Chem. Soc. 1991, 113, 8187;
7. b) V. Snieckus, Chem. Rev. 1990, 90, 879.
8. M. F. Lappert, M. J. Slade. A. Singh, J. L. Atwood, R. D. Rogers, R. Shakir, Z. Am. Chem. Soc. 1983, 105. 302.
9. B. Gehrhus, P. H. Hitchcock, A. R. Kennedy, M. F. Lappert, R. E. Mulvey, P. J. A. Rodger, Z. Organomet. Chem. 1999, 587, 88.
10. P. G. Williard, Q. Y. Liu, Z. Am. Chem. Soc. 1993, 115, 3380.
11. D. R. Armstrong, D. V. Graham, A. R. Kennedy, R. E. Mulvey, C. T. O'Hara, Chem. Eur. J. 2008, 14, 8025.
12. a) G. C. Clososki, C. J. Rohbogner, P. Knochel, Angew. Chem. 2007, 119, 7825;
13. Angew. Chem. Int. Ed. 2007, 46, 7681;
14. b) P. C. Andrews, A. R. Kennedy, R. E. Mulvey, C. L. Raston, B. A. Roberts, R. B. Rowlings, Angew. Chem. 2000, 112, 2036;
15. Angew. Chem. Int. Ed. 2000, 39, 1960.
16. a) Y. Kondo. M. Shilai. M. Uchiyama, T. Sakamoto, J. Am. Chem. Soc. 1999, 121, 3539;
17. b) W. Clegg, S. H. Dale. R.W. Harrington, E. Hevia, G. W. Honeyman, R. E. Mulvey, Angew. Chem. 2006, 118, 2434;
18. Angew. Chem. Int. Ed. 2006, 45, 2374.
19. K. Snégaroff, J. M. L'Helgoual'ch, C. Bentabed-Ababsa, T. T. Nguyen, F. Chevallier. M. Yonehara, M. Uchiyama. A. Derdour, F. Mongin, Chem. Eur. J. 2009, 15, 10280.
20. P. Albores, L. M. Carella. W. Clegg, P. Garcia-Álvarez, A. R. Kennedy, J. Klett, R. E. Mulvey, E. Rentschler, L. Russo, Angew. Chem. 2009, 121, 3367;
21. Angew. Chem. Int. Ed. 2009, 48, 3317.
22. a) J. Garcia-Álvarez. A. R. Kennedy, J. Klett. R. E. Mulvey, Angew. Chem. 2007, 119, 1123;
23. Angew. Chem. Int. Ed. 2007, 46, 1105;
24. b) S. H. Wunderlich. M Kienle. P. Knöchel. Angew. Chem. 2009, 121, 7392;
25. Angew. Chem. Int. Ed. 2009, 48, 7256.
26. M. Uchiyama, H. Naka, Y. Matsumoto, T. Ohwada, J. Am. Chem. Soc. 2004, 126, 10526.
27. R. E. Mulvey, Acc Chem. Res. 2009, 42, 743.
28. a) B. Conway. E. Hevia, J. Garcia-Álvarez, D. V. Graham, A. R. Kennedy, R. E. Mulvey, Chem. Commun. 2007, 5241;
29. b) J. Garcia-Álvarez, E. Hevia. A. R. Kennedy, J. Klett, R. E. Mulvey, Chem. Commun. 2007, 2402.
30. Analogies can be drawn with the "complex-induced proximity effect", see: M. C. Whisler, S. MacNeil, V. Snieckus, P. Beak, Angew. Chem. 2004. 116, 2256;
31. Angew. Chem. Int. Ed. 2004, 43, 2206.
32. B. Conway. J. Garcia-Álvarez. E. Hevia. A. R. Kennedy. R. E. Mulvey, S. D. Robertson, Organometallics 2009, 28, 6462.
33. I. Kamps, D. Bojer, S. A. Hayes, R.J. F. Berger, B. Neumann, N. W. Mitzel, Chem. Eur. J. 2009, 15, 11123.
34. For earlier metalations of TMEDA and PMDETA see, F. H. Köhler, N. Hertkorn, J. Blümel, Chem. Ber. 1987, 120, 2081;
35. V. H. Gessner, C. Strohmann, J. Am. Chem. Soc. 2008, 130, 14412;
36. X. Tian, R. Fröhlich, T. Pape, N. W. Mitzel, Organometallics 2005, 24, 5294;
37. C. Strohmann, V. H. Gessner, Angew. Chem. 2007, 119, 4650;
38. Angew. Chem. Int. Ed. 2007, 46, 4566.
39. 3, CCDC 760700 (2) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
40. L. Barr, A. R. Kennedy, J. G. MacLellan, J. H. Moir, R. E. Mulvey, P. J. A. Rodger, Chem. Commun. 2000, 1757.
41. For examples see, P. C. Andrews. P. J. Nichols, Organometallics 2000, 19, 1277;
42. C. Strohmann. K. Lehmen. K. Wild. D. Schildbach, Organometallics 2002, 21, 3079;
43. I. Kamps, I. Langlitz, A. Mix, B. Neumann, H. G. Stammler, N. W. Mitzel, Dalton Trans. 2009, 8363.
44. M. R. Crimmin, A. G. M. Barrett, M. S. Hill, D. J. MacDougall, M. F. Mahon, P. A. Procopiou, Dalton Trans 2009, 9715.