Lithiation of 2-Me3SiCHRC5H4N(R = H or SiMe3): Influence of solvent on the nature of the product (from X-ray structure determinations) and asymmetric induction. A note on the lithiation of some analogous 3- and 4-methylpyridines

Journal of the Chemical Society, Dalton Transactions

Volumn , Issue 4, 1990, Pages 1161-1172

  Papasergio, Rocco I ^a   Skelton, Brian W ^a   Twiss, Paul ^a   White, Allan H ^a   Raston, Colin L ^b  

^a UNIVERSITY OF WESTERN AUSTRALIA   (Australia)

^b GRIFFITH UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049073300     PISSN: 14727773     EISSN: None     Source Type: Journal    
DOI: 10.1039/DT9900001161     Document Type: Article

References (70)

1. J. L., Wardell, ‘Comprehensive Organometallic Chemistry,’ eds. G. Wilkinson, F. G. A. Stone, and E. W. Abel, Pergamon, Oxford, 1982, vol. 1, ch. 2
2. J. L., Wardell, ‘Chemistry of the Metal Carbon Bond,’ ed. F. R. Hartley, Interscience, 1987, vol. 4, ch. 1
3. B. J., Wakefield, ‘Organolithium Methods,’Academic Press, New York, 1988.
4. W. N., Setzer, P. v. R., Schleyer, Adv. Organomet. Chem., 1985, 24, 353
5. E. M., Kraiser, Tetrahedron, 1983, 39, 2055
6. T., Fujisawa, M., Takeuchi, T., Sato, Chem. Lett., 19821795
7. J. J., Lalonde, D. E., Bergbreiter, M., Newcomb, J. Org. Chem., 1986, 51, 1369
8. N., Kallman, D. B., Collum, J. Am. Chem. Soc., 1987, 109, 7466
9. G., Stork, R. L., Polt, Y., Li, K. N., Houk, J. Am. Chem. Soc., 1988, 110, 8360and refs. therein
10. N. D., Kimpe, P., Sulmon, N., Schamp, Angew. Chem., Int. Ed. Engl., 1985, 24, 881
11. L. M., Engelhardt, W-P., Leung, C. L., Raston, G., Salem, P., Twiss, A. H., White, J. Chem. Soc., Dalton Trans., 19882403
12. M. F., Lappert, L. M., Engelhardt, C. L., Raston, A. H., White, J. Chem. Soc., Chem. Commun., 19821323
13. U., Schumann, J., Kopf, E., Weiss, Angew. Chem., Int. Ed. Engl., 1985, 24, 215
14. G., Frenkel, W. R., Winchester, J. Am. Chem. Soc., 1988, 110, 8721
15. W., Bauer, W. R., Winchester, P. v. R., Schleyer, Organometallics, 1987, 6, 2371
16. For example, W. E., Rhine, J. H., Davis, G. D., Stucky, J. Organomet. Chem., 1977, 134, 139
17. J. J., Stezowski, H., Hoier, D., Wilheilm, T., Clark, P. v. R., Schleyer, J. Chem. Soc., Chem. Commun., 19851263
18. L. M., Engelhardt, R. I., Papasergio, C. L., Raston, A. H., White, J. Chem. Soc., Dalton Trans., 1984311
19. For example, L. M., Englehardt, W-P., Leung, C. L., Raston, A. H., White, J. Chem. Soc., Dalton Trans., 1985337and refs. therein.
20. H. N., Nozaki, T., Aranti, T., Toraya, R., Noyori, Tetrahedron, 1971905
21. L. T., Byrne, L. M., Engelhardt, G. E., Jacobsen, W-P., Leung, R. I., Papasergio, C. L., Raston, B. W., Skelton, P., Twiss, A. H., White, J. Chem. Soc., Dalton Trans., 1989105
22. R. I., Papasergio, C. L., Raston, A. H., White, J. Chem. Soc., Chem. Commun., 19831419
23. D., Colgan, R. I., Papasergio, C. L., Raston, A. H., White, J. Chem. Soc., Chem. Commun., 19841708
24. H., Dietrich, W., Mahdi, R., Knorr, J. Am. Chem. Soc., 1986, 108, 2462
25. L. M., Jackman, L. M., Scarmoutzos, B. D., Smith, P. G., Williard, J. Am. Chem. Soc., 1988, 110, 6058
26. D., Enders, G., Bachstander, K. A. M., Kremer, M., Marsch, K., Harms, G., Boche, Angew. Chem., Int. Ed. Engl., 1988, 27, 1522
27. M. J., Henderson, R. I., Papasergio, C. L., Raston, A. H., White, M. F., Lappert, J. Chem. Soc., Chem. Commun., 1986672
28. L. M., Engelhardt, U., Kynast, C. L., Raston, A. H., White, Angew. Chem., Int. Ed. Engl., 1987, 26, 681
29. L. M., Engelhardt, B. S., Jolly, M. F., Lappert, C. L., Raston, A. H., White, J. Chem. Soc., Chem. Commun., 1988336
30. S. I., Bailey, D., Colgan, L. M., Engelhardt, W-P., Leung, R. I., Papasergio, C. L., Raston, A. H., White, J. Chem. Soc., Dalton Trans., 1986603
31. R. I., Papasergio, C. L., Raston, A. H., White, J. Chem. Soc., Dalton Trans., 19873085
32. P. v. R., Schleyer, R., Hacker, H., Dietrich, W., Mahdi, J. Chem. Soc., Chem. Commun., 1985622
33. S. M., Beshouri, P. E., Fanwick, I. P., Rothwell, J. C., Huffman, Organometallics, 1987, 6, 2498
34. R., Hacker, P. v. R., Schleyer, G., Reber, G., Müller, L., Brandsma, J. Organomet. Chem., 1986, 316, C4
35. E. M., Kaiser, W. R., Thomas, T. E., Synos, J. R., McClure, T. S., Mansour, J. R., Garlich, J. E., Chastain, J. Organomet. Chem., 1981, 213, 405
36. T. S., Mansour, T. C., Wong, E. M., Kaiser, J. Chem. Soc., Perkin Trans. 2, 19852045
37. M. P., Balu, H., Ila, H., Unjappa, Tetrahedron Lett., 1987, 28, 3023
38. T., Konakahara, M., Matsuki, K., Sato, Heterocycles, 1984, 22, 1319
39. T., Konakahara, M., Matsuki, S., Sugimoto, K., Sato, J. Chem. Soc., Perkin Trans. 1, 19871489
40. C., Eaborn, R. A., Shaw, J. Chem. Soc., 19553306
41. T., Konakahara, Y., Takagi, Heterocycles, 1980, 14, 393
42. See for example, D. K., Ellison, R. T., Iwamoto, Tetrahedron Lett., 1983, 24, 31
43. R. L., Bassfield, Y., Houminer, J. Org. Chem., 1983, 48, 2130
44. K., Konishi, H., Matsumoto, K., Saito, K., Takahashi, Bull. Chem. Soc. Jpn., 1983, 58, 2294
45. T., Konakahara, M., Matsuki, S., Sugimoto, K., Sato, J. Chem. Soc., Perkin Trans. 1, 19871489
46. For example, P., Beak, A. I., Myers, Acc. Chem. Res., 1986, 19, 356
47. J. T. B. H., Jastrzebski, G. v., Koten, M., Konijin, C. H., Stam., J. Am. Chem. Soc., 1982, 104, 5490
48. A. A. H. v. d., Zeijden, G. v., Koten, Recl. Trav. Chim. Pays-Bas, 1988, 107, 431
49. J. T. B. H., Jastrzebski, G. v., Koten, K., Goubitz, C., Arlen, M., Pfeffer, J. Organomet. Chem., 1983, 246, C75
50. J. T. B. H., Jastrzebski, G. v., Koten, C., Knaap, A. M. M., Schreurs, J., Kroon, A. L., Soek, Organometallics, 1986, 5, 1551
51. K., Konishi, K., Takahashi, Bull. Chem. Soc. Jpn., 1977, 50, 2512
52. K., Konishi, K., Takahashi, Bull. Chem. Soc. Jpn., 1983, 56, 1612
53. P. v. R., Schleyer, T., Clark, A. J., Kos, G. W., Spitznagel, C., Rhode, D., Arad, K. N., Houk, N. G., Rhodan, J. Am. Chem. Soc., 1984, 106, 6467
54. R. I., Papasergio and C. L., Raston, unpublished work.
55. E. M., Kaiser, J. D., Petty, Synthesis, 1975705
56. H. C., Brown, W. A., Murphey, J. Am. Chem. Soc., 1951, 73, 3308
57. A. D., Miller, C., Osuch, N. N., Goldberg, R., Levine, J. Am. Chem. Soc., 1956, 78, 674
58. A. D., Miller, R., Levine, J. Org. Chem., 1957, 22, 168
59. S., Raynolds, R., Levine, J. Am. Chem. Soc., 1960, 82, 472
60. D. B., Collum, D., Kahne, S. A., Gut, R. T., DePue, F., Mohamadi, R. A., Wanat, J., Clardy, G. v., Duyne, J. Am. Chem. Soc., 1984, 106, 4865
61. L. M., Engelhardt, W-P., Leung, C. L., Raston, P., Twiss, A. H., White, J. Chem. Soc., Dalton Trans., 1984321
62. L. M., Engelhardt, G. E., Jacobsen, P. C., Junk, C. L., Raston, B. W., Skelton, A. H., White, J. Chem. Soc., Dalton Trans., 19881011
63. C., Eaborn, P. B., Hitchcock, J. D., Smith, A. C., Sullivan, J. Chem. Soc., Chem. Commun., 1983827
64. D., Barr, W., Clegg, S. M., Hodgson, R. E., Mulvey, D., Reed, R., Snaith, D. S., Wright, J. Chem. Soc., Chem. Commun., 1988367
65. D., Barr, R., Snaith, R. E., Mulvey, P. G., Perkins, Polyhedron, 1988, 7, 2119and refs. therein.
66. M. F., Lappert, M. J., Slade, A., Singh, J. L., Atwood, R. D., Rogers, R., Shakir, J. Am. Chem. Soc., 1983, 105, 302
67. L. M., Engelhardt, A. S., May, C. L., Raslon, A. H., White, J. Chem. Soc., Dalton Trans., 19831671
68. G., Boche, H., Etzrodt, W., Massa, G., Baum, Angew. Chem., Int. Ed. Engl., 1985, 24, 863
69. J. A. Ibers and W. C. Hamilton (eds.), ‘International Tables for X-Ray Crystallography,’Kynoch Press, Birmingham, 1974, vol. 4.
70. J. M. Stewart and S. R. Hall (eds.), ‘The XTAL System of Crystallographic Programs: User's Manual,’ Technical Report TR-901, Computer Science Centre, University of Maryland, 1983.