Regioselective metalation of a tertiary phosphine. Solution and solid-state structures of an unusual aminobenzyllithium complex

Organometallics

Volumn 18, Issue 20, 1999, Pages 3950-3952

  Clegg, William ^a   Izod, Keith ^a   McFarlane, William ^a   O'Shaughnessy, Paul ^a  

^a NEWCASTLE UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001307831     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9904910     Document Type: Article

References (41)

1. (a) Karsch, H. H.; Müller, G. Chem. Commun. 1984, 569.
2. (b) Blaurock, S.; Kühl, O.; Hey-Hawkins, E. Organometallics 1997, 16, 807.
3. (c) Byrne, L. T.; Engelhardt, L. M.; Jacobsen, G. E.; Leung, W.-P.; Papasergio, R. I.; Raston, C. L.; Skelton, B. W.; Twiss, P.; White, A. H. J. Chem. Soc., Dalton Trans. 1989, 105.
4. (d) Steinborn, D.; Neumann, O.; Weichmann, H.; Heinemann, F. W.; Wagner, J.-P. Polyhedron 1998, 17, 351.
5. (e) Karsch, H. H.; Zellner, K.; Mikulcik, P.; Lachmann, J.; Müller, G. Organometallics 1990, 9, 190.
6. (f) Karsch, H. H.; Richter, R.; Paul, M.; Riede, J. J. Organomet. Chem. 1994, 474, C1.
7. (g) Clegg, W.; Izod, K.; McFarlane, W.; O'Shaughnessy, P. Organometallics 1998, 17, 5231.
8. Clegg, W.; Doherty, S.; Izod, K.; O'Shaughnessy, P. Chem. Commun. 1998, 1129.
9. (a) Jones, F. N.; Hauser, C. R. J. Org. Chem., 1962, 27, 701.
10. (b) Puterbaugh, W. H.; Hauser, C. R. J. Am. Chem. Soc., 1963, 85, 2467.
11. (c) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry, Vol. 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon: Oxford, 1991; pp 42-55.
12. (d) Jastrzebski, J. T. B. H.; van Koten, G.; Lappert, M. F.; Blake, P. C.; Hankey, D. R. Inorg. Synth. 1989, 26, 150.
13. Although 1 may also potentially undergo deprotonation at the site ortho to phosphorus, this is unlikely in such a crowded molecule and has far less precedent.
14. 8-toluene, 25 °C): δ 0.85 (t, J(P,Li) 31.6 Hz).
15. Clegg, W.; Izod, K.; O'Shaughnessy, P. Unpublished results.
16. For examples see: (a) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry, Vol. 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon: Oxford, 1991; pp 15-21. (b) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M., Fleming, I., Eds.; Pergammon Press: New York, 1991; pp 459-485. (c) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471. (d) Rein, K.; Goicoechea-Pappas, M.; Anklekar, T. V.; Hart, G. C.; Smith, G. A.; Gawley, R. E. J. Am. Chem. Soc. 1989, 111, 2211. (e) Katsoulos, G.; Schlosser, M. Tetrahedron Lett. 1993, 34, 6263. (f) Gawley, R. E.; Rein, K.; Chemburkar, S. J. Org. Chem. 1989, 54, 3002. (g) Gawley, R. E.; Chemburkar, S. R.; Smith, A. L.; Anklekar, T. V. J. Org. Chem. 1988, 53, 5381. (h) Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764. (i) Gawley, R. E.; Zhang, Q. Tetrahedron 1994, 50, 6077.
17. For examples see: (a) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry, Vol. 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon: Oxford, 1991; pp 15-21. (b) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M., Fleming, I., Eds.; Pergammon Press: New York, 1991; pp 459-485. (c) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471. (d) Rein, K.; Goicoechea-Pappas, M.; Anklekar, T. V.; Hart, G. C.; Smith, G. A.; Gawley, R. E. J. Am. Chem. Soc. 1989, 111, 2211. (e) Katsoulos, G.; Schlosser, M. Tetrahedron Lett. 1993, 34, 6263. (f) Gawley, R. E.; Rein, K.; Chemburkar, S. J. Org. Chem. 1989, 54, 3002. (g) Gawley, R. E.; Chemburkar, S. R.; Smith, A. L.; Anklekar, T. V. J. Org. Chem. 1988, 53, 5381. (h) Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764. (i) Gawley, R. E.; Zhang, Q. Tetrahedron 1994, 50, 6077.
18. For examples see: (a) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry, Vol. 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon: Oxford, 1991; pp 15-21. (b) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M., Fleming, I., Eds.; Pergammon Press: New York, 1991; pp 459-485. (c) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471. (d) Rein, K.; Goicoechea-Pappas, M.; Anklekar, T. V.; Hart, G. C.; Smith, G. A.; Gawley, R. E. J. Am. Chem. Soc. 1989, 111, 2211. (e) Katsoulos, G.; Schlosser, M. Tetrahedron Lett. 1993, 34, 6263. (f) Gawley, R. E.; Rein, K.; Chemburkar, S. J. Org. Chem. 1989, 54, 3002. (g) Gawley, R. E.; Chemburkar, S. R.; Smith, A. L.; Anklekar, T. V. J. Org. Chem. 1988, 53, 5381. (h) Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764. (i) Gawley, R. E.; Zhang, Q. Tetrahedron 1994, 50, 6077.
19. For examples see: (a) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry, Vol. 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon: Oxford, 1991; pp 15-21. (b) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M., Fleming, I., Eds.; Pergammon Press: New York, 1991; pp 459-485. (c) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471. (d) Rein, K.; Goicoechea-Pappas, M.; Anklekar, T. V.; Hart, G. C.; Smith, G. A.; Gawley, R. E. J. Am. Chem. Soc. 1989, 111, 2211. (e) Katsoulos, G.; Schlosser, M. Tetrahedron Lett. 1993, 34, 6263. (f) Gawley, R. E.; Rein, K.; Chemburkar, S. J. Org. Chem. 1989, 54, 3002. (g) Gawley, R. E.; Chemburkar, S. R.; Smith, A. L.; Anklekar, T. V. J. Org. Chem. 1988, 53, 5381. (h) Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764. (i) Gawley, R. E.; Zhang, Q. Tetrahedron 1994, 50, 6077.
20. For examples see: (a) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry, Vol. 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon: Oxford, 1991; pp 15-21. (b) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M., Fleming, I., Eds.; Pergammon Press: New York, 1991; pp 459-485. (c) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471. (d) Rein, K.; Goicoechea-Pappas, M.; Anklekar, T. V.; Hart, G. C.; Smith, G. A.; Gawley, R. E. J. Am. Chem. Soc. 1989, 111, 2211. (e) Katsoulos, G.; Schlosser, M. Tetrahedron Lett. 1993, 34, 6263. (f) Gawley, R. E.; Rein, K.; Chemburkar, S. J. Org. Chem. 1989, 54, 3002. (g) Gawley, R. E.; Chemburkar, S. R.; Smith, A. L.; Anklekar, T. V. J. Org. Chem. 1988, 53, 5381. (h) Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764. (i) Gawley, R. E.; Zhang, Q. Tetrahedron 1994, 50, 6077.
21. For examples see: (a) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry, Vol. 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon: Oxford, 1991; pp 15-21. (b) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M., Fleming, I., Eds.; Pergammon Press: New York, 1991; pp 459-485. (c) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471. (d) Rein, K.; Goicoechea-Pappas, M.; Anklekar, T. V.; Hart, G. C.; Smith, G. A.; Gawley, R. E. J. Am. Chem. Soc. 1989, 111, 2211. (e) Katsoulos, G.; Schlosser, M. Tetrahedron Lett. 1993, 34, 6263. (f) Gawley, R. E.; Rein, K.; Chemburkar, S. J. Org. Chem. 1989, 54, 3002. (g) Gawley, R. E.; Chemburkar, S. R.; Smith, A. L.; Anklekar, T. V. J. Org. Chem. 1988, 53, 5381. (h) Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764. (i) Gawley, R. E.; Zhang, Q. Tetrahedron 1994, 50, 6077.
22. For examples see: (a) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry, Vol. 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon: Oxford, 1991; pp 15-21. (b) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M., Fleming, I., Eds.; Pergammon Press: New York, 1991; pp 459-485. (c) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471. (d) Rein, K.; Goicoechea-Pappas, M.; Anklekar, T. V.; Hart, G. C.; Smith, G. A.; Gawley, R. E. J. Am. Chem. Soc. 1989, 111, 2211. (e) Katsoulos, G.; Schlosser, M. Tetrahedron Lett. 1993, 34, 6263. (f) Gawley, R. E.; Rein, K.; Chemburkar, S. J. Org. Chem. 1989, 54, 3002. (g) Gawley, R. E.; Chemburkar, S. R.; Smith, A. L.; Anklekar, T. V. J. Org. Chem. 1988, 53, 5381. (h) Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764. (i) Gawley, R. E.; Zhang, Q. Tetrahedron 1994, 50, 6077.
23. For examples see: (a) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry, Vol. 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon: Oxford, 1991; pp 15-21. (b) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M., Fleming, I., Eds.; Pergammon Press: New York, 1991; pp 459-485. (c) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471. (d) Rein, K.; Goicoechea-Pappas, M.; Anklekar, T. V.; Hart, G. C.; Smith, G. A.; Gawley, R. E. J. Am. Chem. Soc. 1989, 111, 2211. (e) Katsoulos, G.; Schlosser, M. Tetrahedron Lett. 1993, 34, 6263. (f) Gawley, R. E.; Rein, K.; Chemburkar, S. J. Org. Chem. 1989, 54, 3002. (g) Gawley, R. E.; Chemburkar, S. R.; Smith, A. L.; Anklekar, T. V. J. Org. Chem. 1988, 53, 5381. (h) Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764. (i) Gawley, R. E.; Zhang, Q. Tetrahedron 1994, 50, 6077.
24. For examples see: (a) Gray, M.; Tinkl, M.; Snieckus, V. In Comprehensive Organometallic Chemistry, Vol. 11; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon: Oxford, 1991; pp 15-21. (b) Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis, Vol. 1; Trost, B. M., Fleming, I., Eds.; Pergammon Press: New York, 1991; pp 459-485. (c) Beak, P.; Zajdel, W. J.; Reitz, D. B. Chem. Rev. 1984, 84, 471. (d) Rein, K.; Goicoechea-Pappas, M.; Anklekar, T. V.; Hart, G. C.; Smith, G. A.; Gawley, R. E. J. Am. Chem. Soc. 1989, 111, 2211. (e) Katsoulos, G.; Schlosser, M. Tetrahedron Lett. 1993, 34, 6263. (f) Gawley, R. E.; Rein, K.; Chemburkar, S. J. Org. Chem. 1989, 54, 3002. (g) Gawley, R. E.; Chemburkar, S. R.; Smith, A. L.; Anklekar, T. V. J. Org. Chem. 1988, 53, 5381. (h) Kopach, M. E.; Meyers, A. I. J. Org. Chem. 1996, 61, 6764. (i) Gawley, R. E.; Zhang, Q. Tetrahedron 1994, 50, 6077.
25. (a) Ahlbrecht, H.; Harbach, J.; Hauk, T.; Kalinowski, H.-O. Chem. Ber. 1992, 125, 1753.
26. (b) Boche, G.; Marsch, M.; Harbach, J.; Harms, K.; Ledig, B.; Schubert, F.; Lohrenz, J. C. W.; Ahlbrecht, H. Chem. Ber. 1993, 126, 1887.
27. (a) Kessar, S. D.; Singh, P.; Vohra, R.; Kaur, N. P.; Singh, K. N. Chem. Commun. 1991, 586.
28. (b) Kessar, S. D.; Singh, P.; Singh, K. N.; Dutt, M. Ibid. 1991, 570.
29. (c) Kessar, S. D.; Singh, P. Chem. Rev. 1997, 97, 721, and references therein.
30. (d) Ebden, M. R.; Simpkins, N. S.; Fox, D. N. A. Tetrahedron Lett. 1995, 36, 8697.
31. -3.
32. (a) Harder, S.; Brandsma, L.; Kanters, J. A.; Duisenberg, A.; van Lenthe, J. H. J. Organomet. Chem. 1991, 420, 143.
33. (b) Pape, A.; Lutz, M.; Müller, G. Angew. Chem., Int. Ed. Engl. 1994, 33, 2281.
34. (c) Fryzuk, M. D.; Giesbrecht, G. R.; Rettig, S. J. Organometallics 1997, 16, 725.
35. (d) Fryzuk, M. D.; Love, J. B.; Rettig, S. J. Chem. Commun. 1996, 2783.
36. (e) Engelhardt, L. M.; Harrowfield, J. M.; Lappert, M, F.; MacKinnon, I. A.; Newton, B. H.; Raston, C. L.; Skelton, B. W.; White, A. H. Chem. Commun. 1986, 846.
37. (f) Froelich, N.; Hitchcock, P. B.; Hu, J.; Lappert, M. F.; Dilworth, J. R. J. Chem. Soc., Dalton Trans. 1996, 1941.
38. A. Bondi, J. Phys. Chem., 1964, 68, 441.
39. Colquhoun, I. J.; McFarlane, H. C. E.; McFarlane, W. J. Chem. Soc. Chem. Commun. 1982, 220; Phosphorus Sulfur 1983, 18, 61.
40. Colquhoun, I. J.; McFarlane, H. C. E.; McFarlane, W. J. Chem. Soc. Chem. Commun. 1982, 220; Phosphorus Sulfur 1983, 18, 61.
41. Reich, H. J.; Gudmundsson, B. O. J. Am. Chem. Soc. 1996, 118, 6074.