Reactivity at the β-Diketiminate Ligand Nacnac- on Titanium(IV) (Nacnac- = [Ar]NC(CH3)CHC(CH 3)N[Ar], Ar = 2,6-[CH(CH3)2]2C 6H3). Diimine-alkoxo and Bis-anilido Ligands Stemming from the Nacnac-Skeleton

Inorganic Chemistry

Volumn 42, Issue 24, 2003, Pages 8003-8010

  Basuli, Falguni ^a   Huffman, John C ^a   Mindiola, Daniel J ^a  

^a INDIANA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BETA DIKETIMINATE; CARBON; CHELATE; IMIDE; KETENE DERIVATIVE; TITANIUM; TITANIUM IMIDE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL; PROTON TRANSPORT; X RAY DIFFRACTION;

EID: 0344154634     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic034853e     Document Type: Article

References (95)

1. (a) McGeachin, S. G. Can. J. Chem. 1968, 46, 1903.
2. (b) Dorman, L. C. Tetrahedron Lett. 1966, 4, 459.
3. (c) Barry, W. J.; Finar, I. L.; Mooney, E. F. Spectrochim. Acta 1965, 21, 1095.
4. (d) Parks, J. E.; Holm, R. H. Inorg. Chem. 1968, 7, 1408.
5. (e) Holm, R. H.; O'Connor, M. J. Proc. Inorg. Chem. 1971, 14, 241.
6. Piers, W. E.; Emslie, D. J. H. Coord. Chem. Rev. 2002, 233, 131.
7. Bourget-Merle, L.; Lappert, M. F.; Severn, J. R. Chem. Rev. 2002, 102, 3031.
8. Stender, M.; Wright, R. J.; Eichler, B. E.; Prust, J.; Olmstead, M. M.; Roesky, H. W.; Power, P. P. J. Chem. Soc., Dalton Trans. 2001, 3465 and references therein.
9. Some examples include: (a) Kakaliou, L.; Scanlon, W. J., IV; Qian, B.; Baek, S. W.; Smith, M. R., III; Motry, D. H. Inorg. Chem. 1999, 38, 5964.
10. (b) Chamberlain, B. M.; Cheng, M.; Moore, D. R.; Ovitt, T. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2001, 123, 3229.
11. (c) Hardman, N. J.; Power, P. P. J. Am. Chem. Soc. 2001, 40. 2474.
12. (d) MacAdams, L. A.; Kim, W.-K.; Liable-Sands, L. M.; Guzei, I. A.; Rheingold, A. L.; Theopold, K. H. Organometallics 2002, 21, 952.
13. (e) Prust, J.; Hohmeister, H.; Stasch, A.; Roesky, H. W.; Magull, J.; Alexopoulos, E.; Usón, I.; Schmidt, H.-G.; Noltemeyer, M. Eur. J. Inorg. Chem. 2002, 2156.
14. (f) Harder, S. Organometallics 2002, 21, 3782.
15. (g) Clegg, W.; Cope, E. K.; Edwards, A. J.; Mair, F. S. Inorg. Chem. 1998, 37, 2317.
16. (h) Qian, B.; Scanlon, W. J.; Smith, M. R., III; Motry, D. H. Organometallics 1999, 18, 1693.
17. Budzelaar, P. H. M.; van Oort, A. B.; Orpen, A. G. Eur. J. Inorg. Chem. 1998, 1485.
18. (a) Kuhn, N.; Lanfermann, H.; Schmitz, P. Liebigs Am. Chem. 1987, 727.
19. (b) Kuhn, N.; Kuhn, A.; Boese, R.; Augart, N. J. Chem. Commun. 1989, 975.
20. (c) Kuhn, N.; Kuhn, A.; Speis, M.; Blaeser, D.; Boese, R. Chem. Ber. 1990, 123, 1301.
21. Spencer, D. J. E.; Reynolds, A. M.; Holland, P. L.; Jazdzewski, B. A.; Duboc-Toia, C.; Le Pape, L. L.; Yokota, S.; Tachi, Y.; Itoh, S.; Tolman, W. B. Inorg. Chem. 2002, 41, 6307 ands references therein.
22. Cheng, M.; Moore, D. R.; Reczek, J. J.; Chamberlain, B. M.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 2001, 123, 8738.
23. Yokota, S.; Tachi, Y.; Itoh, S. Inorg. Chem. 2002, 41, 1342.
24. Yokota, S.; Tachi, Y.; Nishiwaki, N.; Ariga, M.; Itoh, S. Inorg. Chem. 2001, 40, 5316.
25. Davies, I. W.; Marcoux, J.-F.; Wu, J.; Palucki, M.; Corley, E. G.; Robbins, M. A.; Tsou, N.; Ball, R. G.; Dormer, P.; Larsen, R. D.; Reider, P. J. J. Org. Chem. 2000, 65, 4571.
26. Radzewich, C. E.; Coles, M. P.; Jordan, R. F. J. Am. Chem. Soc. 1998, 120, 9384.
27. (a) Cui, C.; Roesky, H. W.; Hao, H.; Schmidt, H.-G.; Noltemeyer, M. Angew. Chem., Int. Ed. 2000, 39, 1815.
28. (b) Hitchcock, P. B.; Hu, J.; Lappert, M. F.; Layh, M.; Liu, D.-S.; Severn, J. R.; Shun, T. Am. Quim. Int. Ed. 1996, 92, 186.
29. (c) Hardman, N. J.; Cui, C.; Roesky, H. W.; Fink, W. H.; Power, P. P. Angew. Chem., Int. Ed. 2001, 40, 2172.
30. (d) Cui, C.; Köpke, S.; Herbst-Irmer, R.; Roesky, H. W.; Noltemeyer, M.; Schmidt, H.-G.; Wrackmeyer, B. J. Am. Chem. Soc. 2001, 123, 9091.
31. (e) Cui, C.; Roesky, H. W.; Schmidt, H.-G.; Noltemeyer, M. Angew. Chem., Int. Ed. 2000, 39, 4531.
32. (f) Hardman, N. J.; Eichler, B. E.; Power, P. P. Chem. Commun. 2000, 1991.
33. (g) Hardman, N. J.; Power, P. P. Inorg. Chem. 2001, 40, 2474.
34. (h) Hardman, N. J.; Power, P. P. Chem. Commun. 2001, 1184.
35. (i) Bai, G. C.; Peng, Y.; Roesky, H. W.; Li, J. Y.; Schmidt, H. G.; Noltemeyer, M. Angew. Chem., Int. Ed. 2003, 42, 1132.
36. (j) Jancik, V.; Peng, Y.; Roesky, H. W.; Li, J. Y.; Neculai, D.; Neculai, A. M.; Herbst-Irmer, R. J. Am. Chem. Soc. 2003, 125, 1452 and references therein.
37. (k) Neculai, A. M.; Neculai, D.; Roesky, H. W.; Magull, J.; Baldus, M.; Andronesi, O.; Jansen, M. Organometallics 2002, 21, 2590.
38. (a) Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 1999, 121, 7270.
39. (b) Holland, P. L.; Tolman, W. B. J. Am. Chem. Soc. 2000, 122, 6331.
40. (c) Randall, D. W.; DeBeer, S.; Holland, P. L.; Hedman, B.; Hodgson, K. O.; Tolman, W. B.; Solomon, E. I. J. Am. Chem. Soc. 2000, 122, 11632.
41. (d) Jazdzewski, B. A.; Holland, P. L.; Pink, M.; Young, V. G., Jr.; Spencer, D. J. E.; Tolman, W. B. Inorg. Chem. 2001, 40, 6097.
42. (a) Dai, X.; Warren, T. H. Chem. Commun. 2001, 1998.
43. (b) Wiencko, H. L.; Kogut, E.; Warren, T. H. Inorg. Chim. Acta 2003, 345, 199.
44. (a) Zhang, S.; Piers, W. E.; Gao, X.; Parvez, M. J. Am. Chem. Soc. 2000, 122, 5499 and references therein.
45. (b) Hayes, P. G.; Piers, W. E.; Lee, L. W. M.; Knight, L. K.; Parvez, M. ; Elsegood, M. R. J.; Clegg, W. Organometallics 2001, 20, 2533.
46. (c) Hayes, P. G.; Piers, W. E.; Parvez, M. J. Am. Chem. Soc. 2003, 125, 5622.
47. (a) Basuli, F.; Bailey, B. C.; Tomaszewski, J.; Huffman, J. C.; Mindiola, D. J. J. Am. Chem. Soc. 2003, 125, 6052.
48. (b) Basuli, F.; Bailey, B. C.; Huffman, J. C.; Mindiola, D. J. Chem. Commun. 2003, 1554.
49. (a) Cheng, M.; Ovitt, T. M.; Hustad, P. D.; Coates, G. W. Polym. Prepr. (Am. Chem. Soc., Div. Polym. Chem.) 1999, 40, 542.
50. (b) Cheng, M.; Attygalle, A. B.; Lobkovsky, E. B.; Coates, G. W. J. Am. Chem. Soc. 1999, 121, 11583.
51. (c) Cheng, M.; Darling, N. A.; Lobkovsky, E. B.; Coates, G. W. Chem. Commun. 2000, 2007.
52. (a) Chisholm, M. H.; Huffman, J. C.; Phomphrai, K. J. Chem. Soc., Dalton Trans. 2001, 222.
53. (b) Chisholm, M. H.; Gallucci, J.; Phomphrai, K. Chem. Commun. 2003, 48.
54. (c) Chisholm, M. H.; Gallucci, J.; Phomphrai, K. Inorg. Chem. 2002, 41, 2785.
55. (a) Richeson, D. S.; Mitchell, J. F.; Theopold, K. H. Organometallics 1989, 8, 2570.
56. (b) Gibson, V. C.; Newton, C.; Redshaw, C.; Solan, G.; White, A. J. P.; Williams, D. J.; Maddox, P. J. Chem. Commun. 1998, 1651.
57. (c) Gibson, V. C.; Newton, C.; Redshaw, C.; Solan, G. A.; White, A. J. P.; Williams, D. J. Eur. J. Inorg. Chem. 2001, 1895.
58. (d) MacAdams, L. A.; Kim, W.-K.; Liable-Sands, L. M.; Guzei, I. A.; Rheingold, A. L.; Theopold, K. H. Organometallics 2002, 21, 952.
59. (e) Kim, W.-K.; Fevola, M. J.; Liable-Sands, L. M.; Rheingold, A. L.; Theopold, K. H. Organometallics 1998, 17, 4541.
60. Radzewich, C. E.; Guzei, I. A.; Jordan, R. F. J. Am. Chem. Soc. 1999, 121, 8673 and references therein.
61. Fekl, U.: Kaminsky, W.; Goldberg, K. I. J. Am. Chem. Soc. 2001, 123, 6423.
62. + at the γ-carbon of the Nacnac backbone has been recently reported: (a) Hitchcock, P. B.; Lappert, M. F.; Nycz, J. E. Chem. Commun. 2003, 1142.
63. (b) Ragogna, P. J.; Bufford, N.; D'eon, M.; McDonald, R. Chem. Commun. 2003, 1052 and references therein. In addition, α-alkoxylithium-β -diimine ligands have been prepared from the reaction of the lithium Nacnac salt and the corresponding ketone: Carey, D. T.; Cope-Eatough, E. K.; Vilaplana-Mafé, E.; Mair, F. S.; Pritchard, R. G.; Warren, J. E.; Woods, R. J. J. Chem. Soc., Dalton Trans. 2003, 1083.
64. (b) Ragogna, P. J.; Bufford, N.; D'eon, M.; McDonald, R. Chem. Commun. 2003, 1052 and references therein. In addition, α-alkoxylithium-β -diimine ligands have been prepared from the reaction of the lithium Nacnac salt and the corresponding ketone: Carey, D. T.; Cope-Eatough, E. K.; Vilaplana-Mafé, E.; Mair, F. S.; Pritchard, R. G.; Warren, J. E.; Woods, R. J. J. Chem. Soc., Dalton Trans. 2003, 1083.
65. Ding, Y.; Hao, H.; Roesky, H. W. Noltemeyer, M.; Schmidt, H.-G. Organometallics 2001, 20, 4806.
66. Basuli, F.; Tomaszewski, J.; Huffman, J. C.; Mindiola, D. J. J. Am. Chem. Soc. 2003, 125, 10170.
67. For a general description of the equipment and techniques used in carrying out this chemistry see: Burger, B. J.; Bercaw, J. E. In Experimental Organometallic Chemistry; Wayda, A. L.; Darensbourg, M. Y., Eds.; ACS Symposium Series 357; American Chemical Society; Washington, DC, 1987; pp 79-98.
68. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518.
69. Taylor, E. C.; McKillop, A.; Hawks, G. H. Org. Synth. 1988, 50, 549.
70. SAINT 6.1; Bruker Analytical X-ray Systems: Madison, WI.
71. SHELXTL-Plus V5.10; Bruker Analytical X-ray Systems: Madison, WI.
72. -1 respectively.
73. tBu ligand see: Carofiglio, T.; Floriani, C.; Chiesi-Villa, A.; Guastini, C. Inorg. Chem. 1989, 28, 4417.
74. A search in the Structural Database shows crystallized free nitriles to have bond lengths between 1.13 and 1.16 Å: Britton, D. Cryst. Struct. Commun. 1979, 8, 667. For a bound nitrile to ah electrophilic early-transition metal center see: Chen, C.-T.; Doerrer, L. H.; Williams, V. C.; Green, M. L. H. J. Chem. Soc., Dalton Trans. 2000, 297.
75. A search in the Structural Database shows crystallized free nitriles to have bond lengths between 1.13 and 1.16 Å: Britton, D. Cryst. Struct. Commun. 1979, 8, 667. For a bound nitrile to ah electrophilic early-transition metal center see: Chen, C.-T.; Doerrer, L. H.; Williams, V. C.; Green, M. L. H. J. Chem. Soc., Dalton Trans. 2000, 297.
76. (a) Cummins, C. C.; Schaller, C. P.; Van Duyne, G. D.; Wolczanski, P. T. ; Chan, A. W.; Hoffmann, R. J. Am. Chem. Soc., 1991, 113, 2985.
77. (b) Bennett, J. L.; Wolczanski, P. T., J. Am. Chem. Soc. 1994, 116, 2179.
78. (a) Wigley, D. E. Prog. Inorg. Chem., 1994, 42, 239.
79. (b) Cummins, C. C. Prog. Inorg. Chem. 1998, 47, 685.
80. (a) Cummins, C. C.; Baxter, S. M.; Wolczanski, P. T. J. Am. Chem. Soc., 1988, 110, 8731.
81. (b) Schaller, C. P.: Wolczanski, P. T. Inorg. Chem. 1993, 32, 131.
82. (c) Schaller, C. P.; Cummins, C. C.; Wolczanski, P. T. J. Am. Chem. Soc. 1996, 118, 591.
83. (d) Bennett, J. L.; Wolczanski, P. T. J. Am. Chem. Soc. 1997, 119, 10696.
84. (e) Schafer, D. F.; Wolczanski, P. T. J. Am. Chem. Soc. 1998, 120, 4881.
85. (f) Gade, L. H.; Mountford, P. Coord. Chem. Rev. 2001, 216-217, 65.
86. (g) Blake, A. J.; Collier, P. E.; Gade, L. H.; Mountford, P.; Lloyd, J.; Pugh, S. M.; Schubart, M.; Skinner, M. E. G. M.; Trösch, D. J. M. Inorg. Chem. 2001, 40, 870.
87. (h) Mountford, P. Perspect. Organomet. Chem. 2003, 28.
88. (i) Blake, A. J.; Collier, P. E.; Gade, L. H.; McPartlin, M.; Mountford, P.; Schubart, M.; Scowen, I. J. Chem. Commun. 1997, 1555.
89. (j) Bashall A.; Collier, P. E.; Gade, L. H.; McPartlin, M.; Mountford, P.; Schubart, M.; Scowen, I. J.; Trösch, D. J. M. Organometallics 2000, 19, 4784.
90. (k) Nikiforov, G. B.; Roesky, H. W.; Magull, J.; Labahn, T.; Vidovic, D. ; Noltemeyer, M.; Schmidt, H.-G.; Hosmane, N. S. Polyhedron 2003, 22, 2669.
91. For some recent examples in the literature see: (a) Brown, S. D.; Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2003, 125, 322 and references therein.
92. (b) Jenkins, D. M.; Betley, T. A.; Peters, J. C. J. Am. Chem. Soc. 2002, 124, 11238.
93. (c) Mindiola, D. J.; Hillhouse, G. H. Chem. Commun. 2002, 1840.
94. Hofmann, P.; Perez-Moya, L. A.; Steigelmann, O.; Riede, J. Organometallics 1992, 11, 1167.
95. For a detailed description of HMQC experiments: Summers, M. F.; Marzilli, L. G.; Bax, A. J. J. Am. Chem. Soc. 1986, 108, 4285.