Reactions of 1,3,5-triazine with organolithium compounds containing trimethylsilyl substituents; X-ray structures of 1,3,5-triaza- and 1,3,5,7-tetraaza-heptatrienyllithium compounds

Journal of the Chemical Society - Dalton Transactions

Volumn , Issue 22, 1999, Pages 4041-4046

  Boesveld, W Marco ^a   Hitchcock, Peter B ^a   Lappert, Michael F ^a  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33749086762     PISSN: 03009246     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907375b     Document Type: Article

References (65)

1. C. Grundmann, Angew. Chem., Int. Ed. Engl., 1963, 2, 309;
2. A. Kreutzberger, Fortschr. Chem. Forsch., 1963, 4, 273.
3. A. Kreutzberger, Angew. Chem., Int. Ed. Engl., 1967, 6, 940.
4. F. C. Schaefer, J. Org. Chem., 1962, 27, 3608.
5. D. R. Armstrong, W. Clegg, M. MacGregor, R. E. Mulvey and P. A. O'Neil, J. Chem. Soc., Chem. Commun., 1993, 608;
6. D. R. Armstrong, K. W. Henderson, M. MacGregor, R. E. Mulvey, M. J. Ross, W. Clegg and P. A. O'Neil, J. Organomet. Chem., 1995, 486, 79;
7. W. Clegg, M. R. J. Elsegood, L. Horsburgh, R. E. Mulvey and M. J. Ross, Chem. Ber., 1997, 130, 621.
8. A. W. Cordes, C. D. Bryan, W. M. Davis, R. H. de Laat, S. H. Glarum, J. D. Goddard, R. C. Haddon, R. G. Hicks, D. K. Kennepohl, R. T. Oakley, S. R. Scott and N. P. C. Westwood, J. Am. Chem. Soc., 1993, 115, 7232.
9. M. F. Lappert and D.-S. Liu, J. Organomet. Chem., 1995, 500, 203.
10. L. S. Cook, G. Prudhoe, N. D. Venayak and B. J. Wakefield, J. Chem. Res. (S), 1982, 113.
11. A. L. Weis, Adv. Heterocycl. Chem., 1985, 38, 91.
12. W. M. Boesveld, P. B. Hitchcock and M. F. Lappert, Chem. Commun., 1997, 2091.
13. B. J. Wakefield, Best Synthetic Methods: Organolithium Methods, Academic Press, London, 1988;
14. L. Brandsma and H. Verkuijsse, Preparative Polar Organometallic Chemistry 1, Springer, Berlin, 1987.
15. M. F. Lappert, P. P. Power, A. R. Sanger and R. C. Srivastava, in Metal and Metalloid Amides, Ellis Horwood, Chichester, 1980.
16. W. N. Setzer and P. v. R. Schleyer, Adv. Organomet. Chem., 1985, 24, 353;
17. K. Gregory, P. v. R. Schleyer and R. Snaith, Adv. Inorg. Chem., 1991, 37, 47;
18. R. E. Mulvey, Chem. Soc. Rev., 1991, 20, 167.
19. F. E. Romesberg and D. B. Collum, J. Am. Chem. Soc., 1992, 114, 2112;
20. D. B. Collum, Acc. Chem. Res., 1993, 26, 227;
21. B. L. Lucht, M. P. Bernstein, J. F. Remenar and D. B. Collum, J. Am. Chem. Soc., 1996, 118, 10707;
22. T. Koizumi, K. Morihashi and O. Kikuchi, Bull. Chem. Soc. Jpn., 1996, 69, 305 and references cited therein.
23. J. Arnold, J. Chem. Soc., Chem. Commun., 1990, 976;
24. J. Arnold, D. Y. Dawson and C. G. Hoffman, J. Am. Chem. Soc., 1993, 115, 2707;
25. U. Piarulli, E. Solari, C. Floriani, A. Chiesi-Villa and C. Rizzoli, J. Am. Chem. Soc., 1996, 118, 3634.
26. H. Homborg and C. L. Teske, Z. Anorg. Allg. Chem., 1985, 527, 45;
27. H. Sugimoto, M. Mori, H. Masuda and T. Taga, J. Chem. Soc., Chem. Commun., 1986, 962;
28. B. Assmann, A. Franken and H. Homborg, Z. Anorg. Allg. Chem., 1995, 621, 1715;
29. B. Latte, B. Assmann and H. Homborg, Z. Anorg. Allg. Chem., 1997, 623, 1281.
30. J. Barker, D. Barr, N. D. R. Barnett, W. Clegg, I. Cragg-Hine, M. G. Davidson, R. P. Davies, S. M. Hodgson, J. A. K. Howard, M. Kilner, C. W. Lehmann, I. Lopez-Solera, R. E. Mulvey, P. R. Raithby and R. Snaith, J. Chem. Soc., Dalton Trans., 1997, 951;
31. M. S. Eisen and M. Kapon, J. Chem. Soc., Dalton Trans., 1994, 3507;
32. D. Stalke, M. Wedler and F. T. Edelmann, J. Organomet. Chem., 1992, 431, C1.
33. T. Gebauer, K. Dehnicke, H. Goesmann and D. Fenske, Z. Naturforsch., Teil B, 1994, 49, 1444.
34. L. M. Engelhardt, G. E. Jacobson, P. C. Junk, C. L. Raston, B. W. Skelton and A. H. White, J. Chem. Soc., Dalton Trans., 1988, 1011;
35. D. Barr, W. Clegg, R. E. Mulvey and R. Snaith, J. Chem. Soc., Chem. Commun., 1984, 469;
36. R. Kempe, A. Spannenberg and S. Brenner, Z. Kristallogr., 1996, 211, 567;
37. M. Polamo and M. Leskelä, J. Chem. Soc., Dalton Trans., 1996, 4345.
38. P. B. Hitchcock, M. F. Lappert and D.-S. Liu, J. Chem. Soc., Chem. Commun., 1994, 1699;
39. H. Gornitzka and D. Stalke, Angew. Chem., Int. Ed. Engl., 1994, 33, 693;
40. H. Gornitzka and D. Stalke, Organometallics, 1994, 13, 4398;
41. F. S. Mair, D. Scully, A. J. Edwards, P. R. Raithby and R. Snaith, Polyhedron, 1995, 14, 2397;
42. D. G. Black, D. C. Swenson, R. F. Jordan and R. D. Rogers, Organometallics, 1995, 14, 3539;
43. B.-J. Deelman, M. F. Lappert, H.-K. Lee, T. C. W. Mak, W.-P. Leung and P.-R. Wei, Organometallics, 1997, 16, 1247.
44. W. M. Boesveld, P. B. Hitchcock and M. F. Lappert, manuscript in preparation
45. W. M. Boesveld and M. F. Lappert, unpublished work; W. M. Boesveld, D.Phil. Thesis, University of Sussex, 1999.
46. R. T. Boeré, R. T. Oakley and R. W. Reed, J. Organomet. Chem., 1987, 331, 161;
47. M. Wedler, F. Knösel, M. Noltemeyer and F. T. Edelmann, J. Organomet. Chem., 1990, 388, 21.
48. M. Schlosser, O. Desponds, R. Lehmann, E. Moret and G. Rauchschwalbe, Tetrahedron, 1993, 49, 10175;
49. A. Beckmann, R. Fröhlich and E.-U. Würthwein, Tetrahedron Lett., 1997, 38, 5481;
50. M. Könemann, G. Erker, R. Fröhlich and E.-U. Würthwein, J. Am. Chem. Soc., 1997, 119, 11155;
51. A. Krol, R. Fröhlich and E.-U. Würthwein, Chem. Commun., 1998, 485.
52. Examples of μ-thf in lithium chemistry: H.-J. Gais, J. Vollhardt, H. Günther, D. Moskau, H. J. Lindner and S. Braun, J. Am. Chem. Soc., 1988, 110, 978;
53. H. Zhang, Y. Wang, A. K. Saxena, A. R. Oki, J. A. Maguire and N. S. Hosmane, Organometallics, 1993, 12, 3933;
54. G. Boche, C. Boie, F. Bosold, K. Harms and M. Marsch, Angew. Chem., Int. Ed. Engl., 1994, 33, 115;
55. W. Clegg, L. Horsburgh, F. M. Mackenzie and R. E. Mulvey, J. Chem. Soc., Chem. Commun., 1995, 2011.
56. J. Barker and M. Kilner, Coord. Chem. Rev., 1994, 133, 219.
57. Recent examples: F. A. Cotton, J. H. Matonic and C. A. Murillo, Inorg. Chem., 1996, 35, 498;
58. F. A. Cotton, S. C. Haefner, J. H. Matonic, X. Wang and C. A. Murillo, Polyhedron, 1997, 16, 541.
59. M. Burke-Laing and M. Laing, Acta Crystallogr., Sect. B, 1976, 32, 3216.
60. W. Hiller, M. Layh and W. Uhl, Angew. Chem., Int. Ed. Engl., 1991, 30, 324.
61. C. Eaborn, P. B. Hitchcock, J. D. Smith and A. C. Sullivan, J. Chem. Soc., Chem. Commun., 1983, 827.
62. J. L. Atwood, T. Fjeldberg, M. F. Lappert, N. T. Luong-Thi, R. Shakir and A. J. Thorne, J. Chem. Soc., Chem. Commun., 1984, 1163.
63. D. Mootz, A. Zinnius and B. Böttcher, Angew. Chem., Int. Ed. Engl., 1969, 8, 378.
64. G. M. Sheldrick, in Crystallographic Computing 3, eds. G. M. Sheldrick, C. Krüger and R. Goddard, Oxford University Press, 1985, p. 175.
65. G. M. Sheldrick, SHELXL 93, University of Göttingen, 1993.