Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Bis(imino)aryl Complex of Nickel(II): N,C,N-Pincer Type Complex, (2,6-(2,6-Et2PhN=CH)2C6H3)NiBr

  • Published : 2008.01.20
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Abstract

The synthesis of a novel N,C,N-type pincer, bis(N-aryl)-2-bromoisophthalaldimine 2,6-(2,6-Et2PhN = CH)2C6H3Br (1) and Ni(1)Br (2) is described. They were characterized by elemental analysis and spectroscopic techniques (IR and 1H NMR). Attempted ethylene polymerization catalyzed by 2 has been futile, leading only to the formation of a small amount of oily oligomers.

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References

  1. Lie, F.; Pak, E. B.; Singh, B.; Jensen, C. M.; Goldman, A. S. J. Am. Chem. Soc. 1999, 121, 4086 https://doi.org/10.1021/ja983460p
  2. Gupta, M.; Hagen, C.; Flesher, R. J.; Kaska, W. C.; Jensen, C. M. Chem. Comm. 1996, 2083
  3. Gupta, M.; Hagen, C.; Kaska, W. C.; Cramer, R. E.; Jensen, C. M. J. Am. Chem. Soc. 1997, 119, 840 https://doi.org/10.1021/ja962560x
  4. Zhang, X.; Emge, T. J.; Ghosh, R.; Goldman, A. S. J. Am. Chem. Soc. 2005, 127, 8250 https://doi.org/10.1021/ja051300p
  5. Cotter, W. D.; Barbour, L.; McNamara, K. L.; Hechter, R.; Lachicotte, R. J. J. Am. Chem. Soc. 1998, 120, 11016 https://doi.org/10.1021/ja980901w
  6. Gagliardo, M.; Rodriguez, G.; Dam, H. H.; Lutz, M.; Spek, A. L.; Havenith, R. W. A.; Coppo, P.; De Cola, L.; Hartl, F.; Van Klink, G. P. M.; van Koten, G. Inorg. Chem. 2006, 45, 2143 https://doi.org/10.1021/ic051967c
  7. Olsson, D.; Nilsson, P.; Masnaouy, M. E.; Wendt, O. F. Dalton Trans. 2005, 11, 1924
  8. Ohff, M.; Ohff, A.; Van der Boom, M. E.; Milstein, D. J. Am. Chem. Soc. 1997, 119, 11687 https://doi.org/10.1021/ja9729692
  9. Lee, H. M.; Zeng, J. Y.; Hu, C.; Lee, M. Inorg. Chem. 2004, 43, 6822 https://doi.org/10.1021/ic049492x
  10. Jung, I. G.; Son, S. U.; Park, K. H.; Chung, K.-C.; Lee, J. W.; Chung, Y. K. Organometallics 2003, 22, 4715 https://doi.org/10.1021/om030371z
  11. Yoon, M. S.; Ryu, D.; Kim, J.; Ahn, K. H. Organometallics 2006, 25, 2409 https://doi.org/10.1021/om0601246
  12. Rybtchinski, B.; Vigalok, A.; Ben-David, Y.; Milstein, D. J. Am. Chem. Soc. 1996, 118, 12406 https://doi.org/10.1021/ja962253r
  13. Van der Boom, M. E.; Kraatz, H. B.; Hassner, L.; Ben-David, Y.; Milstein, D. Organometallics 1999, 18, 3873 https://doi.org/10.1021/om990282f
  14. Rybtchinski, B.; Milstein, D. J. Am. Chem. Soc. 1999, 121, 4528 https://doi.org/10.1021/ja990339p
  15. Van der Boom, M. E.; Liou, S. Y.; Ben-David, Y.; Vigalok, A.; Milstein, D. Angew. Chem., Int. Ed. Engl. 1997, 36, 625 https://doi.org/10.1002/anie.199706251
  16. van der Boom, M. E.; Liou, S.; Shimon, L. J. W.; Ben-David, Y.; Milstein, D. Inorg. Chim. Acta 2004, 357, 4015 https://doi.org/10.1016/j.ica.2004.06.002
  17. Soro, B.; Stoccoro, S.; Minghetti, G.; Zucca, A.; Cinellu, M. A.; Manassero, M.; Gladiali, S. Inorg. Chim. Acta 2006, 359, 1879 https://doi.org/10.1016/j.ica.2005.07.045
  18. Weng, W.; Parkin, S.; Ozerov, O. V. Organometallics 2006, 25, 5345 https://doi.org/10.1021/om060464r
  19. Albrecht, M.; van Koten, G. Angew. Chem., Int. Ed. 2001, 40, 3750 https://doi.org/10.1002/1521-3773(20011015)40:20<3750::AID-ANIE3750>3.0.CO;2-6
  20. Albrecht, M.; Rodriguez, G.; Schoenmaker, J.; van Koten, G. Org. Lett. 2000, 2, 3461 https://doi.org/10.1021/ol006484l
  21. Steenwinkel, P.; Gossage, R. A.; van Koten, G. Chem. Eur. J. 1998, 4, 759 https://doi.org/10.1002/(SICI)1521-3765(19980515)4:5<759::AID-CHEM759>3.0.CO;2-K
  22. Guillena, G.; Kruithof, C. A.; Casado, M. A.; Egmond, M. R.; van Koten, G. J. Organomet. Chem. 2003, 668, 3 https://doi.org/10.1016/S0022-328X(02)02099-5
  23. van der Boom, M. E.; Milstein, D. Chem. Rev. 2003, 103, 1759 https://doi.org/10.1021/cr960118r
  24. Pugh, D.; Danopoulos, A. A. Coord. Chem. Rev. 2007, 251, 610 https://doi.org/10.1016/j.ccr.2006.08.001
  25. Moulton, C. J.; Shaw, B. L. J. Chem. Soc., Dalton Trans. 1976, 1020
  26. Creaser, C. S.; Kaska, W. C. Inorg. Chim. Acta 1978, 30, L325 https://doi.org/10.1016/S0020-1693(00)88995-1
  27. Rimml, H.; Venanzi, L. M. J. Organomet. Chem. 1983, 259, C6 https://doi.org/10.1016/0022-328X(83)85164-X
  28. Bennett, M. A.; Jin, H.; Willis, A. C. J. Organomet. Chem. 1993, 451, 249 https://doi.org/10.1016/0022-328X(93)83032-Q
  29. Kraatz, H.-B.; Milstein, D. J. Organomet. Chem. 1995, 488, 223 https://doi.org/10.1016/0022-328X(94)00027-A
  30. Gagliardo, M.; Havenith, R. W. A.; van Klink, G.; van Koten, G. J. Organometal. Chem. 2006, 691, 4411 https://doi.org/10.1016/j.jorganchem.2006.01.035
  31. Poverenov, E.; Leitus, G.; Shimon, L. J. W.; Milstein, D. Organometallics 2005, 24, 5937 https://doi.org/10.1021/om050637x
  32. Singleton, J. T. Tetrahedron 2003, 59, 1837 https://doi.org/10.1016/S0040-4020(02)01511-9
  33. Benito- Garagorri, D.; Bocokic, V.; Mereiter, K.; Kirchner, K. Organometallics 2006, 25, 3817 https://doi.org/10.1021/om060289e
  34. Goldman, A. S.; Roy, A. H.; Huang, Z.; Ahuja, R.; Schinski, W.; Brookhart, M. Science 2006, 312, 257 https://doi.org/10.1126/science.1123787
  35. Takenaka, K.; Minakawa, M.; Uozumi, Y. J. Am. Chem. Soc. 2005, 127, 12273 https://doi.org/10.1021/ja052780n
  36. Seul, J. M.; Park, S. J. Chem. Soc., Dalton Trans. 2002, 1153
  37. Ryu, S. Y.; Kim, H.; Kim, H. S.; Park, S. J. Organomet. Chem. 1999, 592, 194 https://doi.org/10.1016/S0022-328X(99)00511-2
  38. Park, S. Bull. Korean Chem. Soc. 2001, 22, 1410
  39. Park, S. Bull. Korean Chem. Soc. 2002, 23, 132 https://doi.org/10.5012/bkcs.2002.23.1.132
  40. Park, S. Bull. Korean Chem. Soc. 2001, 22, 15
  41. Hoogervorst, W. J.; Goubitz, K.; Fraanje, J.; Lutz, M.; Spek, A. L.; Ernsting, J. M.; Elsevier, C. J. Organometallics 2004, 23, 4550 https://doi.org/10.1021/om049619q
  42. Vila, J. M.; Gayoso, M.; Pereira, T.; Lopez Torres, M.; Fernandez, J. J.; Fernandez, A.; Ortigueira, J. M. J. Organomet. Chem. 1996, 506, 165 https://doi.org/10.1016/0022-328X(95)05691-H
  43. Fossey, J. S.; Richards, C. J. Organometallics 2002, 21, 5259 https://doi.org/10.1021/om020566r
  44. Hoogervorst, W. J.; Elsevier, C. J.; Lutz, M.; Spek, A. L. Organometallics 2001, 20, 4437 https://doi.org/10.1021/om010447w
  45. Hoogervorst, W. J.; Koster, A. L.; Lutz, M.; Spek, A. L.; Elsevier, C. J. Organometallics 2004, 23, 1161 https://doi.org/10.1021/om0343972
  46. Oakley, S. H.; Coogan, M. P.; Arthur, R. J. Organometallics 2007, 26, 2285 https://doi.org/10.1021/om070059f
  47. Stol, M.; Snelders, D. J. M.; Godbole, M. D.; Havenith, R. W. A.; Haddleton, D.; Clarkson, G.; Lutz, M.; Spek, A. L.; van Klink, G. P. M.; van Koten, G. Organometallics 2007, 26, 3985 https://doi.org/10.1021/om061055y
  48. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: Oxford, 1988
  49. Mataka, S.; Liu, G.; Sawada, T.; Kurisu, M.; Tashiro, M. Bull. Chem. Soc. Jpn. 1994, 67, 1113 https://doi.org/10.1246/bcsj.67.1113
  50. Mataka, S.; Liu, G.; Sawada, T.; Tori-i, A.; Tashiro, M. J. Chem. Research, Syn. 1995, 10, 410
  51. Lee, D. H.; Park, S. submitted for publication

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