Yttrium complexes incorporating the chelating diamides {ArN(CH 2)xNAr}2- (Ar = C6H 3-2,6-iPr2, x = 2, 3) and their unusual reaction with phenylsilane

Dalton Transactions

Volumn , Issue 7, 2004, Pages 1083-1096

  Avent, Anthony G ^a   Cloke, F Geoffrey N ^a   Elvidge, Benjamin R ^a   Hitchcock, Peter B ^a  

^a UNIVERSITY OF SUSSEX   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

APPROXIMATION THEORY; CATALYSTS; CHELATION; COMPLEXATION; HYDROGEN; IONS; MONOMERS; OLIGOMERS; POLYMERIZATION; PROTONS; REACTION KINETICS; RECRYSTALLIZATION (METALLURGY); SYNTHESIS (CHEMICAL);

DONOR ATOMS; DONOR SOLVENTS; LEWIS ACIDS; LIGANDS;

YTTRIUM COMPOUNDS;

EID: 2342539834     PISSN: 14779226     EISSN: None     Source Type: Journal    
DOI: 10.1039/B400149D     Document Type: Article

References (87)

1. (a) P. L. Watson, J. Am. Chem. Soc., 1982, 104, 337;
2. (b) G. Jeske, H. Lauke, H. Mauermann, P. N. Swepston, H. Schumann and T. J. Marks, J. Am. Chem. Soc., 1985, 107, 8091;
3. (c) G. Jeske, L. E. Schock, P. N. Swepston, H. Schumann and T. J. Marks, J. Am. Chem. Soc., 1985, 107, 8103;
4. (d) P. L. Watson and G. W. Parshall, Ace. Chem. Res., 1985, 18, 51.
5. (a) W J. Evans, Adv. Orgcmomet. Chem., 1985, 24, 131;
6. (b) H. Schumann, J. A. Meesemarktscheffel and L. Esser, Chem. Rev., 1995, 95, 865.
7. (a) F. T. Edelmann, Angew. Chem., Int. Ed. Engl., 1995, 34, 2466;
8. (b) G. J. P. Britovsek, V. C. Gibson and D. F. Wass, Angew. Chem., Int. Ed. Engl., 1999, 38, 428;
9. (c) W. E. Piers and D. J. H. Emslie, Coord. Chem. Rev., 2002, 233, 131;
10. (d) F. T. Edelmann, D. M. M. Freckmann and H. Schumann, Chem. Rev., 2002, 102, 1851;
11. (e) P. Mountford and B. D. Ward, Chem. Commun., 2003, 1797;
12. (f) J. Okuda, Dalton Trans., 2003, 2367.
13. R. Kempe, Angew. Chem., Int. Ed. Engl., 2000, 39, 468.
14. F. G. N. Cloke, B. R. Elvidge, P. B. Hitchcock and V. M. E. Lamarche, J. Chem. Soc., Dalton Trans., 2002, 2413.
15. (a) J. D. Scollard, D. H. McConville and J. J. Vittal, Organometallics, 1995, 14, 5478;
16. (b) J. D. Scollard and D. H. McConville, J. Am. Chem. Soc., 1996, 118, 10008;
17. (c) J. D. Scollard, D. H. McConville, N. C. Payne and J. J. Vittal, Macromolecules, 1996, 29, 5241;
18. (d) J. D. Scollard, D. H. McConville and J. J. Vittal, Organometallics, 1997, 16, 4415.
19. D. D. Graf, W. M. Davis and R. R. Schrock, Organometallics, 1998, 17, 5820.
20. T. I. Gountchev and T. D. Tilley, Organometallics, 1999, 18, 2896.
21. (a) M. D. Fryzuk, J. B. Love and S. J. Rettig, Chem. Commun., 1996, 2783;
22. (b) M. D. Fryzuk, J. B. Love and S. J. Rettig, J. Am. Chem. Soc. 1997, 119, 9071.
23. M. D. Fryzuk, P. H. Yu and B. O. Patrick, Can. J. Chem., 2001, 79, 1194.
24. F. Estler, G. Eickerling, E. Herdtweck and R. Anwander, Organometallics, 2003, 22, 1212.
25. M. E. G. Skinner and P. Mountford, J. Chem. Soc., Dalton Trans., 2002, 1694.
26. (a) M. F. Lappert and R. Pearce, J. Chem. Soc., Chem. Commun., 1973, 126;
27. (b) K. C. Hultzsch, H. P. Spaniol and J. Okuda, Angew. Chem., Int. Ed, 1999, 38, 227.
28. D. C. Bradley, J. S. Ghotra and F. A. Hart, J. Chem. Soc., Dalton Trans., 1973, 1021.
29. 3) can conveniently be prepared from the metal and mercury(II) iodide in a sealed ampoule at high temperature. Full synthetic details can be found in the ESI.
30. F. T. Edelmann, in Synthetic Methods of Organometattic and Inorganic Chemistry, ed. G. Brauer and W. A. Herrmann, Georg Thieme Verlag, Stuttgart, 1997.
31. C. Callaghan, G. K. B. Clentsmith, F. G. N. Cloke, P. B. Hitchcock, J. F. Nixon and D. M. Vickers, Organometallics, 1999, 18, 793; full synthetic details for potassium menthoxide can be found in the ESI.
32. Shortly after our initial disclosure an alternative synthesis of this potassium salt along with synthetic data on certain yttrium and lutetium complexes was published: P. W. Roesky, Organometallics, 2002, 21, 4756.
33. Z. W. Xie, Z. X. Liu, F. Xue, Z. Y. Zhang and T. C. W. Mak, J. Organomet. Chem., 1997, 542, 285.
34. K. H. Denhaan, J. L. Deboer, J. H. Teuben, A. L. Spek, B. Kojicprodic, G. R. Hays and R. Huis, Organometallics, 1986, 5, 1726.
35. G. Jeske, H. Lauke, H. Mauermann, P. N. Swepston, H. Schumann and T. J. Marks, J. Am. Chem. Soc., 1985, 107, 8091.
36. 1H NMR spectrum.
37. R. Duchateau, C. T. van Wee, A. Meetsma, P. T. van Duijnen and J. H. Teuben, Organometallics, 1996, 15, 2279.
38. R. Duchateau, T. Tuinstra, E. A. C. Brussee, A. Meetsma, P. T. van Duijnen and J. H. Teuben, Organometallics, 1997, 16, 3511.
39. A figure depicting this variable-temperature NMR study can be found in the ESI.
40. A. Mandel and J. Magull, Z. Anorg. Allg. Chem., 1997, 623, 1542.
41. A. Mandel and J. Magull, Z. Anorg. Allg. Chem., 1996, 622, 1913.
42. S. Bambirra, M. J. R. Brandsma, E. A. C. Brussee, A. Meetsma, B. Hessen and J. H. Teuben, Organometallics, 2000, 19, 3197.
43. M. Booij, A. Meetsma and J. H. Teuben, Organometallics, 1991, 10, 3246.
44. M. F. Lappert, P. P. Power, A. R. Sanger and R. C. Srivastava, Metal and Metalloid Amides, Ellis Horwood, Chichester, 1980.
45. M. Westerhausen, M. Hartmann, A. Pfitzner and W. Schwarz, Z. Anorg. Allg. Chem., 1995, 621, 837.
46. Tables of selected bond lengths, angles and crystallographic data as well as full details of all structure determinations and results of the refinements for all of the molecular structures presented herein can be found in the ESI.
47. M. Westerhausen, M. Hartmann, A. Pfitzner and W. Schwarz, Z. Anorg. Allg. Chem., 1995, 621, 837.
48. H. Schumann, E. C. E. Rosenthal, G. Kociok-köhn, G. A. Molander and J. Winterfeld, J. Organomet. Chem., 1995, 496, 233.
49. 1H NMR study of 8 is included in the ESI.
50. 2-4-Me) can be found in the ESI.
51. W. J. Evans and B. L. Davis, Chem. Rev., 2002, 102, 2119.
52. The dihedral angle defined by N(1)-N(2)-N(3)-N(4), for example, is 78.2°.
53. K. C. Hultzsch, T. P. Spaniol and J. Okuda, Organometallics, 1997, 16, 4845.
54. H. Schumann, E. Palamidis and J. Loebel, J. Organomet. Chem., 1990, 390, 45; J. Guan, Q. Shen, S. Jin and Y. Lin, Polyhedron, 1994, 13, 1695.
55. H. Schumann, E. Palamidis and J. Loebel, J. Organomet. Chem., 1990, 390, 45; J. Guan, Q. Shen, S. Jin and Y. Lin, Polyhedron, 1994, 13, 1695.
56. J. W. Lauher and R. Hoffmann, J. Am. Chem. Soc., 1976, 98, 1729.
57. G. K. B. Clentsmith, F. G. N. Cloke, J. C. Green, J. Hanks, P. B. Hitchcock and J. F. Nixon, Angew. Chem., Int. Ed., 2003, 42, 1038.
58. T. Grob, G. Seybert, W. Massa, K. Harms and K. Dehnicke, Z. Anorg. Allg. Chem., 2000, 626, 1361.
59. W. J. Evans, J. H. Meadows, A. L. Wayda, W. E. Hunter and J. L. Atwood, J. Am. Chem. Soc., 1982, 104, 2015.
60. W. J. Evans, J. H. Meadows and T. P. Hanusa, J. Am. Chem. Soc., 1984, 106, 4454.
61. W. J. Evans, D. K. Drummond, T. P. Hanusa and R. J. Doedens, Organometallics, 1987, 6, 2279.
62. -1 region, in which yttrium hydrides generally come into resonance, and were thus inconclusive.
63. The value of x could have been found by depression of the freezing point experiments in benzene, however it was not possible to produce enough sample to carry out this experiment due to the low yield of the reaction.
64. P. B. Hitchcock, M. F. Lappert and R. G. Smith, Inorg. Chim, Acta, 1987, 139, 183.
65. W. T. Klooster, L. Brammer, C. J. Schaverien and P. H. M. Budzelaar, J. Am. Chem. Soc., 1999, 121, 1381.
66. K. B. Aubrecht, K. Chang, M. A. Hillmyer and W. B. Tolman, J. Polym. Sci. Part A: Polym. Chem., 2001, 39, 284.
67. C. M. Forsyth, S. P. Nolan and T. J. Marks, Organometallics, 1991, 10, 2543.
68. P. F. Fu, L. Brard, Y. W. Li and T. J. Marks, J. Am. Chem. Soc., 1995, 117, 7157.
69. A. Z. Voskoboynikov, I. N. Parshina, A. K. Shestakova, K. P. Butin, I. P. Beletskaya, L. G. Kuzmina and J. A. K. Howard, Organometallics, 1997, 16, 4041.
70. T. I. Gountchev and T. D. Tilley, Organometallics, 1999, 18, 5661.
71. (a) N. W. Mitzel, A. Schier, H. Beruda and H. Schmidbaur, Chem. Ber./Recl., 1992, 125, 1053;
72. (b) N. Mitzel, A. Schier and H. Schmidbaur, Chem. Ber./Recl., 1992, 125, 2711;
73. (c) N. W. Mitzel, J. Riede, A. Schier, M. Paul and H. Schmidbaur, Chem. Ber./Recl., 1993, 126, 2027;
74. (d) N. W. Mitzel, K. Angermaier and H. Schmidbaur, Organometallics, 1994, 13, 1762;
75. (e) N. W. Mitzel, K. Angermaier and H. Schmidbaur, Chem. Ber., 1994, 127, 841.
76. (a) T. D. Tilley, A. Zalkin, R. A. Andersen and D. H. Templeton, Inorg. Chem., 1981, 20, 551;
77. (b) H. C. Aspinall, D. C. Bradley, M. B. Hursthouse, K. D. Sales, N. P. C. Walker and B. Hussain, J. Chem. Soc., Dalton Trans., 1989, 623.
78. Such behaviour towards higher olefins is well documented for lanthanide complexes. One possible explanation is the formation of an yttrium allyl complex that is unreactive towards olefin insertion, e.g.: (a) W. J. Evans, C. A. Seibel and J. W. Ziller, J. Am. Chem. Soc., 1998, 120, 6745; (b) W. J. Evans, M. A. Johnston, C. H. Fujimoto and J. Greaves, Organometallics, 2000, 19, 4258; (c) C. P. Casey, T. Y. Lee, J. A. Tunge and D. W. Carpenetti, J. Am. Chem. Soc., 2001, 123, 10762; (d) C. P. Casey, J. A. Tunge and M. A. Fagan, J. Organomet. Chem., 2002, 663, 91.
79. Such behaviour towards higher olefins is well documented for lanthanide complexes. One possible explanation is the formation of an yttrium allyl complex that is unreactive towards olefin insertion, e.g.: (a) W. J. Evans, C. A. Seibel and J. W. Ziller, J. Am. Chem. Soc., 1998, 120, 6745; (b) W. J. Evans, M. A. Johnston, C. H. Fujimoto and J. Greaves, Organometallics, 2000, 19, 4258; (c) C. P. Casey, T. Y. Lee, J. A. Tunge and D. W. Carpenetti, J. Am. Chem. Soc., 2001, 123, 10762; (d) C. P. Casey, J. A. Tunge and M. A. Fagan, J. Organomet. Chem., 2002, 663, 91.
80. Such behaviour towards higher olefins is well documented for lanthanide complexes. One possible explanation is the formation of an yttrium allyl complex that is unreactive towards olefin insertion, e.g.: (a) W. J. Evans, C. A. Seibel and J. W. Ziller, J. Am. Chem. Soc., 1998, 120, 6745; (b) W. J. Evans, M. A. Johnston, C. H. Fujimoto and J. Greaves, Organometallics, 2000, 19, 4258; (c) C. P. Casey, T. Y. Lee, J. A. Tunge and D. W. Carpenetti, J. Am. Chem. Soc., 2001, 123, 10762; (d) C. P. Casey, J. A. Tunge and M. A. Fagan, J. Organomet. Chem., 2002, 663, 91.
81. Such behaviour towards higher olefins is well documented for lanthanide complexes. One possible explanation is the formation of an yttrium allyl complex that is unreactive towards olefin insertion, e.g.: (a) W. J. Evans, C. A. Seibel and J. W. Ziller, J. Am. Chem. Soc., 1998, 120, 6745; (b) W. J. Evans, M. A. Johnston, C. H. Fujimoto and J. Greaves, Organometallics, 2000, 19, 4258; (c) C. P. Casey, T. Y. Lee, J. A. Tunge and D. W. Carpenetti, J. Am. Chem. Soc., 2001, 123, 10762; (d) C. P. Casey, J. A. Tunge and M. A. Fagan, J. Organomet. Chem., 2002, 663, 91.
82. (a) L. Titcomb, Synth. Pages, 2001, 30;
83. (b) L. Titcomb, Synth. Pages, 2001, 28.
84. G. M. Sheldrick, SHELXS-86, Program for Crystal Structure Analysis, University of Göttingen, Germany, 1986.
85. G. M. Sheldrick, SHELXS-97, Program for Crystal Structure Analysis, University of Göttingen, Germany, 1997.
86. L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565.
87. The broad nature of this spectrum precluded any meaningful integration.