Reversible skeletal transmetalations of inorganic rings: Isolation of aluminatophosphazenes, a zwitterionic phosphazene, and a donor-stabilized alumazine-phosphazene hybrid cation

Inorganic Chemistry

Volumn 44, Issue 19, 2005, Pages 6789-6798

  Rivard, Eric ^a   Ragogna, Paul J ^a,c   McWilliams, Andrew R ^a,b   Lough, Alan J ^a   Manners, Ian ^a  

^a UNIVERSITY OF TORONTO   (Canada)

^b RYERSON UNIVERSITY   (Canada)

^c UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 25144508520     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic0509938     Document Type: Article

References (89)

1. (a) Cui, C.; Roesky, H. W.; Schmidt, H.-G.; Noltemeyer, M.; Hao, H.; Cimpoesu, F. Angew, Chem., Int. Ed. 2000, 39, 4272.
2. (b) Scheschkewitz, D.; Gornitzka, A. H.; Schoeller, W. W.; Bourissou, D.; Bertrand, G. Science 2002, 295, 1880.
3. (c) Hardman, N. J.; Power, P. P.; Gorden, J. D.; Macdonald, C. L. B.; Cowley, A. H. Chem. Commun. 2001, 1866.
4. (d) Ni, Y.; Lough, A. J.; Rheingold, A. L.; Manners, I. Angew. Chem., Int. Ed. Engl. 1995, 34, 998.
5. (e) Guo, C.-Y.; Kirchmeier, R. L.; Shreeve, J. M. J. Am. Chem. Soc. 1991, 113, 9000.
6. (f) Barclay, T. M.; Cordes, A. W.; Goddard, J. D.; Mawhinney, R. C.; Oakley, R. T.; Preuss, K. E.; Reed, R. W. J. Am. Chem. Soc. 1997, 119, 12136.
7. (g) Brownridge, S.; Du, H.-B.; Fairhurst, S. A.; Haddon, R. C.; Oberhammer, H.; Parsons, S.; Passmore, J.; Schriver, M. J.; Sutcliffe, L. H.; Westwood, N. P. C. J. Chem. Soc., Dalton Trans. 2000, 3365.
8. (h) Burford, N.; Cameron, T. S.; Conroy, K. D.; Ellis, B.; Lumsden, M.; Macdonald, C. L. B.; Phillips, A. D.; Ragogna, P. J.; Schurko, R. W.; Walsh, D.; Wasylishen, R. E. J. Am. Chem. Soc. 2002, 124, 14012.
9. (i) Haiduc, I. The Chemistry of Inorganic Ring Systems, Part I and II; Wiley-Interscience: Toronto, 1970.
10. (j) Roesky, H. W. Inorg. Chem. 2004, 43, 7284.
11. (k) Martin, D.; Baceiredo, A.; Gornitzka, H.; Schoeller, W. W.; Bertrand, G.; Angew. Chem., Int. Ed. 2005, 44, 1700.
12. For selected examples of aluminum-based heterocyclic catalysts, see: (a) Coles, M. P.; Jordan, R. F. J. Am. Chem. Soc. 1997, 119, 8125.
13. (b) Ihara, E.; Young, V. G., Jr.; Jordan, R. F. J. Am. Chem. Soc. 1998, 120, 8277.
14. (c) Bruce, M.; Gibson, V. C.; Redshaw, C.; Solan, G. A.; White, A. J. P.; Williams, D. J. Chem. Commun. 1998, 2523.
15. (d) Cameron, P. A.; Gibson, V. C.; Redshaw, C.; Segal, J. A.; Bruce, M. D.; White, A. J. P.; Williams, D. J. Chem. Commun. 1999, 1883.
16. (e) Duchateau, R.; Meetsma, A.; Teuben, J. H. Chem. Commun. 1996, 223.
17. (f) Korolev, A. V.; Ihara, E.; Guzei, I. A.; Young, V. G., Jr.; Jordan, R. F. J. Am. Chem. Soc. 2001, 123, 8291.
18. (g) Yu, R.-C.; Hung, C.-H.; Huang, J.-H.; Lee, H.-Y.; Chen, J.-T. Inorg. Chem. 2002, 41, 6450.
19. (h) Cameron, P. A.; Gibson, V. C.; Irvine, D. J. Angew. Chem., Int. Ed. 2000, 39, 2141.
20. For selected examples of transition metal-based heterocyclic catalysts, see: (a) Johnson, L. K.; Killian, C. M.; Brookhart, M. J. Am. Chem. Soc. 1995, 117, 6414.
21. (b) Scollard, J. D.; McConville, D. H. J. Am. Chem. Soc. 1996, 118, 10008.
22. (c) Baumann, R.; Davis, W. M.; Schrock, R. R. J. Am. Chem. Soc. 1997, 119, 3830.
23. (d) Mehrkhodavandi, P.; Schrock, R. R. J. Am. Chem. Soc. 2001, 123, 10746.
24. (e) Hagihara, H.; Shiono, T.; Ikeda, T. Macromolecules 1998, 31, 3184.
25. (f) Jayaratne, K. C.; Sita, L. R. J. Am. Chem. Soc. 2000, 122, 958.
26. (g) Betley, T. A.; Peters, J. C. Angew. Chem., Int. Ed. 2003, 42, 2385.
27. (h) Gibson, V. C.; Spitzmesser, S. K. Chem. Rev. 2003, 103, 283.
28. Manners, I. Angew. Chem., Int. Ed. Engl. 1996, 35, 1602.
29. (a) Allcock, H. R.; Kugel, R. L. J. Am. Chem. Soc. 1965, 87, 4216.
30. (b) Allcock, H. R. J. Inorg. Organomet. Polym. 1992, 2, 197.
31. (c) Manners, I.; Allcock, H. R.; Renner, G.; Nuyken, O. J. Am. Chem. Soc. 1989, 111, 5478.
32. (d) Dodge, J. A.; Manners, I.; Allcock, H. R.; Renner, G.; Nuyken, O. J. Am. Chem. Soc. 1990, 112, 1268.
33. (e) Gates, D. P.; Manners, I. J. Chem. Soc., Dalton Trans. 1997, 2525.
34. (a) Gates, D. P.; Edwards, M.; Liable-Sands, L. M.; Rheingold, A. L.; Manners, I. J. Am. Chem. Soc. 1998, 120, 3249.
35. (b) McWilliams, A. R.; Gates, D. P.; Edwards, M.; Liable-Sands, L. M.; Guzei, I.; Rheingold, A. L.; Manners, I. J. Am. Chem. Soc. 2000, 122, 8848.
36. (c) Liang, M.; Manners, I. J. Am. Chem. Soc. 1991, 113, 4044.
37. Gates, D. P.; Ziembinski, R.; Rheingold, A. L.; Haggerty, B. S.; Manners, I. Angew. Chem., Int. Ed. Engl. 1994, 33, 2277.
38. Gates, D. P.; Liable-Sands, L. M.; Yap, G. P. A.; Rheingold, A. L.; Manners, I. J. Am. Chem. Soc. 1997, 119, 1125.
39. Gates, D. P.; McWilliams, A. R.; Ziembinski, R.; Liable-Sands, L. M.; Guzei, I. A.; Yap, G. P. A.; Rheingold, A. L.; Manners, I. Chem. Eur. J. 1998, 4, 1489.
40. (a) Fagan, P. J.; Nugent, W. A. J. Am. Chem. Soc. 1988, 110, 2310.
41. (b) Jolliffe, J. M.; Kelly, P. F.; Woollins, J. D. J. Chem. Soc., Dalton Trans. 1989, 2179.
42. (c) Kuhn, N.; Kuhn, A.; Lewandowski, J.; Speis, M. Chem. Ber. 1991, 124, 2197.
43. (d) Breen, T. L.; Stephan, D. W. Organometallics 1997, 16, 365.
44. (e) Ashe, A. J., III; Fang, X.; Kampf, J. F. Organometallics 2001, 20, 2109.
45. For a brief communication on some of this work, see; (a) McWilliams, A. R.; Rivard, E.; Lough, A. J.; Manners, I. Chem. Commun. 2002, 1102.
46. For an early report on a four-membered N-P zwitterionic ring system, see: (b) Niecke, E.; Kröher, R.; Pohl, S. Angew. Chem., Int. Ed. 1977, 16, 864.
47. 3 produces a complex mixture of partially methylated phosphazene rings: Harris, P. J.; Jackson, L. A. Organometallics 1983, 2, 1477.
48. 3 in toluene is δ = 86.6: Bochmann, M.; Sarsfield, M. J. Organometallics 1998, 17, 5908.
49. Cocco, L.; Eyman, D. P. J. Organomet. Chem. 1979, 179, 1.
50. For related Al-N-P heterocycles, see: (a) Hasselbring, R.; Roesky, H. W.; Heine, A.; Stalke, D.; Sheldrick, G. M. Z. Naturforsch. 1994, 49B, 43.
51. (b) Burford, N.; LeBlanc, D. J. Inorg. Chem. 1999, 38, 2248.
52. (c) Lawson, G. T.; Jacob, C.; Steiner, A. Eur. J. Inorg. Chem. 1999, 1881.
53. Burrow, R. A.; Farrar, D. H.; Honeyman, C. H. Acta Crystallogr. 1994, C50, 681.
54. 3 (4-10 equiv).
55. Qian, B.; Ward, D. L.; Smith, M. R., III. Organometallics 1998, 17, 3070.
56. 31P NMR resonances (26-28 ppm). All attempts to isolate pure products from these reactions have been frustrated by the extreme reactivity of the possibly cationic aluminum product.
57. For examples of the use of skeletal substitution chemistry in organic synthesis, see: (a) Nakamoto, M.; Tilley, T. D. Organometalllcs 2001, 20, 5515.
58. (b) Nitschke, J. R.; Tilley, T. D. J. Organomet. Chem. 2002, 666, 15.
59. (c) Takahashi, T.; Ishikawa, M.; Huo, S. J. Am. Chem. Soc. 2002, 124, 388.
60. Cotton, F. A.; Wilkinson, G.; Murillo, C. A.; Bochmann, M. Advanced Inorganic Chemistry, 6th ed.; Wiley-Interscience: Toronto, 1999; p 392.
61. Cyr, P. W.; Rettig, S. J.; Patrick, B. O.; James, B. R. Organometallics 2002, 21, 4672.
62. 2 spin system.
63. For related work, see: (a) Well, M.; Jones, P. G.; Schmutzler, R. J. Fluorine Chem. 1991, 53, 261.
64. (b) Kaukorat, T.; Jones, P. G.; Schmutzler, R. Heteratom. Chem. 1991, 2, 8129.
65. (c) Schlak, O.; Schmutzler, R.; Schiebel, H.-M.; Wazeer, M. I. M.; Harris, R. K. J. Chem. Soc., Dalton Trans. 1974, 2153.
66. (d) Hahn, H.; Toifl, E.; Meindl, W.; Utvary, K. Monatsh. Chem. 1984, 115, 881.
67. (e) Galle, K.; Utvary, K. Monatsh. Chem. 1988, 119, 174.
68. Rivard, E.; McWilliams, A. R.; Lough, A. J.; Manners, I. Acta Crystallogr. 2002, 58C, 114 and references therein.
69. Kitashita, K.; Hagiwara, R.; Ito, Y.; Tamada, O. Solid State Sci. 2000, 2, 237.
70. Klapötke, T. M. J. Chem. Soc., Dalton Trans. 1997, 553.
71. For salient discussions involving the nature of Al-O-C bonding, see: (a) Barron, A. R. Polyhedron 1995, 22, 3197.
72. (b) Burford, N. Coord. Chem. Rev. 1992, 112, 1.
73. An unusually short Al-O bond (1.659(3) Å) involving a tetracoordinate Al center has recently been reported. The exact nature of this bond is still under investigation: Neculai, D.; Roesky, H. W.; Neculai, A. M.; Magull, J.; Walfort, B.; Stalke, D. Angew. Chem., Int. Ed. 2002, 41, 4294.
74. 2U as the ethylating reagent.
75. For cationic aluminum heterocycles, see: (a) Radzewicz, C. E.; Coles, M. P.; Jordan, R. F. J. Am. Chem. Soc. 1998, 120, 9384.
76. (b) Coslédan, F.; Hitchcock, P. B.; Lappert, M. F. Chem. Commun. 1999, 705.
77. (c) Dagorne, S.; Guzei, I. A.; Coles, M. P.; Jordan, R. F. J. Am. Chem. Soc. 2000, 122, 274.
78. (d) Cameron, P. A.; Gibson, V. C.; Redsahw, C.; Segal, J. A.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Dalton Trans. 2002, 415.
79. (e) Schmidt, J. A. R.; Arnold, J. Organometallics 2002, 21, 2306.
80. Klosin, J.; Roof, G. R.; Chen, E. Y.-X.; Abboud, K. A. Organometallics 2000, 19, 4684.
81. Spitzmesser, S. K.; Gibson, V. C. J. Organomet. Chem. 2003, 673, 95.
82. (a) Pappalardo, D.; Tedesco, C.; Pellecchia, C. Eur. J. Inorg. Chem. 2002, 621.
83. (b) see refs 18 and 33.
84. Cameron, P. A.; Gibson, V. C.; Redshaw, C.; Segal, J. A.; Solan, G. A.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Dalton Trans. 2001, 1472.
85. - anion are notoriously difficult to crystallize as they tend to form "clathrate"-type oils.
86. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518.
87. Bartlett, R. A.; Rasika Dias, H. V.; Flynn, K. M.; Olmstead, M. M.; Power, P. P. J. Am. Chem. Soc. 1987, 109, 5699.
88. Otwinowski, Z.; Minor, W. Methods Enzymol. 1997, 276, 307.
89. Sheldrick, G. M. SHELXTL-Windows NT. V.6.12, Bruker Analytical X-ray Systems, Inc.: Madison, WI, 2001.