Cyclometalated compounds. XI.1 single and double cyclometalations of poly(pyrazolylmethyl)benzenes

Organometallics

Volumn 17, Issue 16, 1998, Pages 3487-3496

  Hartshorn, Chris M ^a   Steel, Peter J ^a  

^a UNIVERSITY OF CANTERBURY   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000977228     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om9800851     Document Type: Article

References (82)

1. Part X: O'Keefe, B. J.; Steel, P. J. Organometallics, in press.
2. (a) Constable, E. C. Polyhedron 1984, 3, 1037.
3. (b) Omae, I. J. Organomet. Chem. Libr. 1986, 18, 1.
4. (c) Omae, I. Coord. Chem. Rev. 1988, 83, 137.
5. (d) Ryabov, A. D. Chem. Rev. 1990, 90, 403.
6. Ryabov, A. D. Synthesis 1985, 233.
7. Bruce, D. W. J. Chem. Soc., Dalton Trans. 1993, 2983. Buey, J.; Espinet, P. J. Organomet. Chem. 1996, 507, 137 and references therein.
8. Bruce, D. W. J. Chem. Soc., Dalton Trans. 1993, 2983. Buey, J.; Espinet, P. J. Organomet. Chem. 1996, 507, 137 and references therein.
9. Navarro-Ranninger, C.; Lopez-Solera, I; Rodriguez, J.; Garcia-Ruano, J. L.; Raithby, P. R.; Masaguer, J. R.; Alonso, C. J. Med. Chem. 1993, 36, 3795. Navarro-Ranninger, C.; Lopez-Solera, I.; Gonzalez, V. M.; Perez, J. M.; Alvarez-Valdes, A.; Martin, A.; Raithby, P. R.; Masaguer, J. R.; Alonso, C. Inorg. Chem. 1996, 35, 5181.
10. Navarro-Ranninger, C.; Lopez-Solera, I; Rodriguez, J.; Garcia-Ruano, J. L.; Raithby, P. R.; Masaguer, J. R.; Alonso, C. J. Med. Chem. 1993, 36, 3795. Navarro-Ranninger, C.; Lopez-Solera, I.; Gonzalez, V. M.; Perez, J. M.; Alvarez-Valdes, A.; Martin, A.; Raithby, P. R.; Masaguer, J. R.; Alonso, C. Inorg. Chem. 1996, 35, 5181.
11. (a) Canty, A. J.; Minchin, N. J.; Skelton, B. W.; White, A. H. J. Chem. Soc., Dalton Trans. 1987, 1477.
12. (b) Albert, J.; Ceder, R. M.; Gomez, M.; Granell, J.; Sales, J. Organometallics 1992, 11, 1536.
13. (c) Hiraki, K.; Nakashima, M.; Uchiyama, T.; Fuchita, Y. J. Organomet. Chem 1992, 428, 249.
14. (d) Barro, J.; Granell, J.; Sainz, D.; Sales, J.; Font-Bardia, M.; Solans, X. J. Organomet. Chem. 1993, 456, 147.
15. (e) Alonso, M. T.; Juanes, O.; de Mendoza, J.; Rodnguez-Ubis, J. C. J. Organomet. Chem. 1994, 484, 19.
16. (f) Krylova, L. F.; Dulepova, N. V. Zh. Neorg. Khim. 1994, 39, 2022.
17. (g) Tollari, S.; Palmisano, G.; Demartin, F.; Grassi, M.; Magnaghi, S.; Cenini, S. J. Organomet. Chem. 1995, 488, 79.
18. (h) Fuchita, Y.; Yoshinaga, Y.; Kusaba, H.; Mori, M.; Hiraki, K.; Takehara, K. Inorg. Chim. Acta 1995, 239, 125.
19. Constable, E. C.; Henney, R. P. G.; Leese, T. A.; Tocher, D. A. J. Chem. Soc., Dalton Trans. 1990, 443. Constable, E. C.; Dunne, S J.; Rees, D. G.; Schmitt, C. X. J. Chem. Soc., Chem. Commun. 1996, 1169. Constable, E. C.; Cargill Thompson, A. M. W. New J. Chem. 1996, 20, 65.
20. Constable, E. C.; Henney, R. P. G.; Leese, T. A.; Tocher, D. A. J. Chem. Soc., Dalton Trans. 1990, 443. Constable, E. C.; Dunne, S J.; Rees, D. G.; Schmitt, C. X. J. Chem. Soc., Chem. Commun. 1996, 1169. Constable, E. C.; Cargill Thompson, A. M. W. New J. Chem. 1996, 20, 65.
21. Constable, E. C.; Henney, R. P. G.; Leese, T. A.; Tocher, D. A. J. Chem. Soc., Dalton Trans. 1990, 443. Constable, E. C.; Dunne, S J.; Rees, D. G.; Schmitt, C. X. J. Chem. Soc., Chem. Commun. 1996, 1169. Constable, E. C.; Cargill Thompson, A. M. W. New J. Chem. 1996, 20, 65.
22. Alsters, P. L.; Engel, P. F.; Hogerheide, M. P.; Copijn, M.; Spek, A. L.; van Koten, G. Organometallics 1993, 12, 1831. Garcia-Herbosa, G.; Munoz, A.; Miguel, D.; Garcia-Granda, S. Organometallics 1994, 13, 1775. Lucena, N.; Casabo, J.; Escriche, L.; Sanchez-Castello, G.; Teixidor, F.; Kivekas, R.; Sillanpaa, R. Polyhedron 1996, 15, 3009. Jouaiti, A.; Geoffroy, M.; Collin, J.-P. Inorg. Chim. Acta 1996, 245, 69 and references therein.
23. Alsters, P. L.; Engel, P. F.; Hogerheide, M. P.; Copijn, M.; Spek, A. L.; van Koten, G. Organometallics 1993, 12, 1831. Garcia-Herbosa, G.; Munoz, A.; Miguel, D.; Garcia-Granda, S. Organometallics 1994, 13, 1775. Lucena, N.; Casabo, J.; Escriche, L.; Sanchez-Castello, G.; Teixidor, F.; Kivekas, R.; Sillanpaa, R. Polyhedron 1996, 15, 3009. Jouaiti, A.; Geoffroy, M.; Collin, J.-P. Inorg. Chim. Acta 1996, 245, 69 and references therein.
24. Alsters, P. L.; Engel, P. F.; Hogerheide, M. P.; Copijn, M.; Spek, A. L.; van Koten, G. Organometallics 1993, 12, 1831. Garcia-Herbosa, G.; Munoz, A.; Miguel, D.; Garcia-Granda, S. Organometallics 1994, 13, 1775. Lucena, N.; Casabo, J.; Escriche, L.; Sanchez-Castello, G.; Teixidor, F.; Kivekas, R.; Sillanpaa, R. Polyhedron 1996, 15, 3009. Jouaiti, A.; Geoffroy, M.; Collin, J.-P. Inorg. Chim. Acta 1996, 245, 69 and references therein.
25. Alsters, P. L.; Engel, P. F.; Hogerheide, M. P.; Copijn, M.; Spek, A. L.; van Koten, G. Organometallics 1993, 12, 1831. Garcia-Herbosa, G.; Munoz, A.; Miguel, D.; Garcia-Granda, S. Organometallics 1994, 13, 1775. Lucena, N.; Casabo, J.; Escriche, L.; Sanchez-Castello, G.; Teixidor, F.; Kivekas, R.; Sillanpaa, R. Polyhedron 1996, 15, 3009. Jouaiti, A.; Geoffroy, M.; Collin, J.-P. Inorg. Chim. Acta 1996, 245, 69 and references therein.
26. Beley, M.; Collin, J.-P.; Sauvage, J.-P. Inorg. Chem. 1993, 32, 4539. Barigelletti, F.; Flamigni, L.; Guadigli, M.; Juris, A.; Beley, M.; Chodorowski-Kimmes, S.; Collin, J.-P.; Sauvage, J.-P. Inorg. Chem. 1996, 35, 136 and references therein.
27. Beley, M.; Collin, J.-P.; Sauvage, J.-P. Inorg. Chem. 1993, 32, 4539. Barigelletti, F.; Flamigni, L.; Guadigli, M.; Juris, A.; Beley, M.; Chodorowski-Kimmes, S.; Collin, J.-P.; Sauvage, J.-P. Inorg. Chem. 1996, 35, 136 and references therein.
28. (a) Izumi, T.; Kasahara, A. Bull. Yamagata Univ., Eng. 1979, 15, 213.
29. (b) Espinet, P.; Garcia, G.; Herrero, F. J.; Jeannin, Y.; PhilocheLevisalles, M. Inorg. Chem. 1989, 28, 4207.
30. (c) Caygill, G.B.; Hartshorn, R. M.; Steel, P. J. J. Organomet. Chem. 1990, 382, 455.
31. (d) Caygill, G. B.; Steel, P. J. J. Organomet. Chem. 1990, 395, 359.
32. (e) Jouaiti, A.; Geoffroy, M.; Bernardinelli, G. Tetrahedron Lett. 1993, 34, 3413.
33. (f) Selvakumar, K.; Vancheesan, S. Polyhedron 1996, 15, 2535.
34. (g) Vila, J. M.; Gayoso, M.; Lopez Torres, M.; Fernandez, J. J.; Fernandez, A.; Ortigueira, J. M.; Bailey, N. A.; Adams, H. J. Organomet. Chem. 1996, 511, 129.
35. (h) Lopez, C.; Bosque, R. J. Organomet. Chem. 1996, 524, 247.
36. (a) Trofimenko, S. J. Am. Chem. Soc. 1971, 93, 1808.
37. (b) Phillips, I. G.; Steel, P. J. J. Organomet. Chem. 1991, 410, 247.
38. (c) Chakladar, S.; Paul, P.; Venkatsubramanian, K.; Nag, K. J. Chem. Soc., Dalton Trans. 1991, 2669.
39. (d) Chakladar, S.; Paul, P.; Nag, K. Polyhedron 1991, 10, 1513.
40. (e) Chakladar, S.; Paul, P.; Mukherjee, A. K.; Dutta, S. K.; Nanda, K. K.; Podder, D.; Nag, K. J. Chem. Soc., Dalton Trans. 1992, 3119.
41. (f) Loeb, S. J.; Shimizu, G. K. J. Chem. Soc., Chem. Commun. 1993, 1395.
42. (g) Vila, J. M.; Gayoso, M.; Pereira, M. T.; Torres, M. L.; Fernandez, J. J.; Fernandez, A.; Ortigueira, J. M. J. Organomet. Chem. 1996, 506, 165.
43. (h) Steenwinkel, P.; James, S. L.; Grove, D. M.; Kooijman, H.; Spek, A. L.; van Koten, G. Organometallics 1997, 16, 513.
44. (i) Lydon, D. P.; Rourke, J. P. Chem. Commun. 1997, 1741.
45. Hartshorn, C. M.; Steel, P. J. Aust. J. Chem. 1995, 48, 1587.
46. Hartshorn, C. M.; Steel, P. J. Angew. Chem., Int. Ed. Engl. 1996, 35, 2655.
47. Hartshorn, C. M.; Steel, P. J. Chem. Commun. 1997, 541.
48. van Koten, G. Pure Appl. Chem. 1989, 61, 1681 and references therein. Hogerheide, M. P.; Grove, D. M.; Boersma, J.; Jastrzebski, J. T. B. H.; Kooijman, H.; Spek, A. L.; van Koten, G. Chem. Eur. J. 1995, 1, 343. Djukic, J.-P.; Maisse, A.; Pfeffer, M.; de Cian, A.; Fischer, J. Organometallics 1997, 16, 657.
49. van Koten, G. Pure Appl. Chem. 1989, 61, 1681 and references therein. Hogerheide, M. P.; Grove, D. M.; Boersma, J.; Jastrzebski, J. T. B. H.; Kooijman, H.; Spek, A. L.; van Koten, G. Chem. Eur. J. 1995, 1, 343. Djukic, J.-P.; Maisse, A.; Pfeffer, M.; de Cian, A.; Fischer, J. Organometallics 1997, 16, 657.
50. van Koten, G. Pure Appl. Chem. 1989, 61, 1681 and references therein. Hogerheide, M. P.; Grove, D. M.; Boersma, J.; Jastrzebski, J. T. B. H.; Kooijman, H.; Spek, A. L.; van Koten, G. Chem. Eur. J. 1995, 1, 343. Djukic, J.-P.; Maisse, A.; Pfeffer, M.; de Cian, A.; Fischer, J. Organometallics 1997, 16, 657.
51. Canty, A. J.; Honeyman, R. T.; Skelton, B. W.; White, A. H. J. Organomet. Chem. 1990, 389, 277.
52. van der Made, A. W.; van der Made, R. H. J. Org. Chem. 1993, 58, 1262.
53. There is evidence of a slight tetrahedral distortion from square planarity around the palladium, as the mean plane defined by Pd1 (deviation from the plane of 0.023(2) Å), Cl1 (-0.046(3)), C2 (-0.058-(5)), N12 (0.040(5)), and N32 (0.040(5)) shows alternating displacement of the donor atoms above and below the plane.
54. Steffen, W. L.; Palenik, G. J. Inorg. Chem. 1976, 15, 2432.
55. Watson, A. A.; House, D. A.; Steel, P. J. Aust. J. Chem. 1995, 48, 1549 and references therein.
56. Collin, J.-P.; Beley, M.; Sauvage, J.-P.; Bangelletti, F. Inorg. Chim. Acta 1991, 186, 91. Constable, E. C.; Hannon, M. J. Inorg. Chim. Acta 1993, 211, 101. Ward, M. D. J. Chem. Soc., Dalton Trans. 1994, 3095. Bardwell, D. A.; Jeffrey, J. C.; Schatz, E.; Tilley, E. E.; Ward, M. D. J. Chem. Soc., Dalton Trans. 1995, 825.
57. Collin, J.-P.; Beley, M.; Sauvage, J.-P.; Bangelletti, F. Inorg. Chim. Acta 1991, 186, 91. Constable, E. C.; Hannon, M. J. Inorg. Chim. Acta 1993, 211, 101. Ward, M. D. J. Chem. Soc., Dalton Trans. 1994, 3095. Bardwell, D. A.; Jeffrey, J. C.; Schatz, E.; Tilley, E. E.; Ward, M. D. J. Chem. Soc., Dalton Trans. 1995, 825.
58. Collin, J.-P.; Beley, M.; Sauvage, J.-P.; Bangelletti, F. Inorg. Chim. Acta 1991, 186, 91. Constable, E. C.; Hannon, M. J. Inorg. Chim. Acta 1993, 211, 101. Ward, M. D. J. Chem. Soc., Dalton Trans. 1994, 3095. Bardwell, D. A.; Jeffrey, J. C.; Schatz, E.; Tilley, E. E.; Ward, M. D. J. Chem. Soc., Dalton Trans. 1995, 825.
59. Collin, J.-P.; Beley, M.; Sauvage, J.-P.; Bangelletti, F. Inorg. Chim. Acta 1991, 186, 91. Constable, E. C.; Hannon, M. J. Inorg. Chim. Acta 1993, 211, 101. Ward, M. D. J. Chem. Soc., Dalton Trans. 1994, 3095. Bardwell, D. A.; Jeffrey, J. C.; Schatz, E.; Tilley, E. E.; Ward, M. D. J. Chem. Soc., Dalton Trans. 1995, 825.
60. Crabtree, R. H.; Hamilton, D. G. Adv. Organomet. Chem. 1988, 28, 299. Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1. Kawamoto, T.; Nagasawa, I.; Kuma, H.; Kushi, Y. Inorg. Chem. 1996, 35, 2427.
61. Crabtree, R. H.; Hamilton, D. G. Adv. Organomet. Chem. 1988, 28, 299. Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1. Kawamoto, T.; Nagasawa, I.; Kuma, H.; Kushi, Y. Inorg. Chem. 1996, 35, 2427.
62. Crabtree, R. H.; Hamilton, D. G. Adv. Organomet. Chem. 1988, 28, 299. Brookhart, M.; Green, M. L. H.; Wong, L.-L. Prog. Inorg. Chem. 1988, 36, 1. Kawamoto, T.; Nagasawa, I.; Kuma, H.; Kushi, Y. Inorg. Chem. 1996, 35, 2427.
63. Dani, P.; Karlen, T.; Gossage, R. A.; Smeets, W. J. J.; Spek, A. L.; van Koten, G. J. Am. Chem. Soc. 1997, 119, 11317.
64. See, for example: Rasmussen, S. C.; Ronco, S. E.; Mlsna, D. A.; Billadeau, M. A.; Pennington, W. T.; Kolis, J. W.; Petersen, J. D. Inorg. Chem. 1995, 34, 821. Gerli, A.; Reedijk, J.; Lakin, M. T.; Spek, A. L. Inorg. Chem. 1995, 34, 1836.
65. See, for example: Rasmussen, S. C.; Ronco, S. E.; Mlsna, D. A.; Billadeau, M. A.; Pennington, W. T.; Kolis, J. W.; Petersen, J. D. Inorg. Chem. 1995, 34, 821. Gerli, A.; Reedijk, J.; Lakin, M. T.; Spek, A. L. Inorg. Chem. 1995, 34, 1836.
66. Constable, E. C. Prog. Inorg. Chem. 1994, 42, 67.
67. Shirin, Z.; Pramanik, A.; Ghost, P.; Mukherjee, R. Inorg. Chem. 1996, 35, 3431. Bhambri, S.; Tocher, D. A. J. Organomet. Chem. 1996, 507, 291.
68. Shirin, Z.; Pramanik, A.; Ghost, P.; Mukherjee, R. Inorg. Chem. 1996, 35, 3431. Bhambri, S.; Tocher, D. A. J. Organomet. Chem. 1996, 507, 291.
69. The unreacted excess ligand was recovered with good efficiency from the reaction mixture.
70. The palladium atoms each have approximately square planar coordination to the N, C, N, Cl donor set, with a slight tetrahedral distortion from this geometry. This can again be seen in the alternating pattern above and below the plane defined by Pd and the four coordinated atoms. The trans coordination angles for the four C-Pd-Cl sets (average angle 178.5(3)°) are less distorted from linearity than the N-Pd-N sets (average angle 171.1(3)°).
71. Intille, G. M.; Pfluger, C. E.; Baker, W. A. Cryst. Struct. Commun. 1973, 2, 217. Arack, R.; Zetterberg, K. Organometallics 1987, 6, 1230. Davies, J. A.; Pinkerton, A. A.; Syed, R.; Vilmer, V. J. Chem. Soc., Chem. Commun. 1988, 47. Albano, V. G.; Castellari, C., Cucciolito, M. E.; Panunzi, A.; Vitagliano, A. Organometallics 1990, 9, 1269. Perreault, D.; Drouin, M.; Michel, A.; Harvey, P. D. Inorg. Chem. 1992, 31, 2740.
72. Intille, G. M.; Pfluger, C. E.; Baker, W. A. Cryst. Struct. Commun. 1973, 2, 217. Arack, R.; Zetterberg, K. Organometallics 1987, 6, 1230. Davies, J. A.; Pinkerton, A. A.; Syed, R.; Vilmer, V. J. Chem. Soc., Chem. Commun. 1988, 47. Albano, V. G.; Castellari, C., Cucciolito, M. E.; Panunzi, A.; Vitagliano, A. Organometallics 1990, 9, 1269. Perreault, D.; Drouin, M.; Michel, A.; Harvey, P. D. Inorg. Chem. 1992, 31, 2740.
73. Intille, G. M.; Pfluger, C. E.; Baker, W. A. Cryst. Struct. Commun. 1973, 2, 217. Arack, R.; Zetterberg, K. Organometallics 1987, 6, 1230. Davies, J. A.; Pinkerton, A. A.; Syed, R.; Vilmer, V. J. Chem. Soc., Chem. Commun. 1988, 47. Albano, V. G.; Castellari, C., Cucciolito, M. E.; Panunzi, A.; Vitagliano, A. Organometallics 1990, 9, 1269. Perreault, D.; Drouin, M.; Michel, A.; Harvey, P. D. Inorg. Chem. 1992, 31, 2740.
74. Intille, G. M.; Pfluger, C. E.; Baker, W. A. Cryst. Struct. Commun. 1973, 2, 217. Arack, R.; Zetterberg, K. Organometallics 1987, 6, 1230. Davies, J. A.; Pinkerton, A. A.; Syed, R.; Vilmer, V. J. Chem. Soc., Chem. Commun. 1988, 47. Albano, V. G.; Castellari, C., Cucciolito, M. E.; Panunzi, A.; Vitagliano, A. Organometallics 1990, 9, 1269. Perreault, D.; Drouin, M.; Michel, A.; Harvey, P. D. Inorg. Chem. 1992, 31, 2740.
75. Intille, G. M.; Pfluger, C. E.; Baker, W. A. Cryst. Struct. Commun. 1973, 2, 217. Arack, R.; Zetterberg, K. Organometallics 1987, 6, 1230. Davies, J. A.; Pinkerton, A. A.; Syed, R.; Vilmer, V. J. Chem. Soc., Chem. Commun. 1988, 47. Albano, V. G.; Castellari, C., Cucciolito, M. E.; Panunzi, A.; Vitagliano, A. Organometallics 1990, 9, 1269. Perreault, D.; Drouin, M.; Michel, A.; Harvey, P. D. Inorg. Chem. 1992, 31, 2740.
76. Hartshorn, C. M. Ph.D. Thesis, University of Canterbury, 1996.
77. Polyakov, V. A.; Ryabov, A. D. J. Chem. Soc., Dalton Trans. 1986, 589.
78. Evans, I. P.; Spencer, A.; Wilkinson, G. J. Chem. Soc., Dalton Trans. 1973, 204.
79. Sullivan, B. P.; Calvert, J. M.; Meyer, T. J. Inorg. Chem. 1980, 19, 1404.
80. von Braun, J.; Nelles, J. Chem. Ber. 1934, 67, 1094.
81. Sheldrick, G. M. Acta Crystallogr., Sect. A 1990, 46, 467.
82. Sheldrick, G. M. SHELXL-93; University of Gottingen, Germany, 1993.