Synthesis, complexation, and coordination oligomerization of 1,8-pyrazine-capped 5,12-dioxocyclams

Inorganic Chemistry

Volumn 42, Issue 14, 2003, Pages 4346-4354

  Hegedus, Louis S ^a   Sundermann, Michael J ^a   Dorhout, Peter K ^a  

^a Department of Ecosystem Science and Sustainability   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2,6 BIS(BROMOMETHYL)PYRAZINE; AMINE; CARBONYL DERIVATIVE; COPPER COMPLEX; CYCLAM DERIVATIVE; FERROMAGNETIC MATERIAL; MACROCYCLIC COMPOUND; METAL COMPLEX; METHYLMETHOXY 5,12 DIOXOCYCLAM; NITROGEN; OXYGEN DERIVATIVE; PYRAZINE DERIVATIVE; RHENIUM; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; COMPLEX FORMATION; CRYSTAL STRUCTURE; CYCLIC POTENTIOMETRY; ELECTRON SPIN RESONANCE; GEOMETRY; INFRARED SPECTROSCOPY; MAGNETISM; MICROWAVE IRRADIATION; OXIDATION REDUCTION REACTION; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

BRIDGED COMPOUNDS; COPPER; CRYSTALLOGRAPHY, X-RAY; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE SPECTROSCOPY; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MAGNETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRAZINES; RHODIUM; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0037560086     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic030090j     Document Type: Article

References (69)

1. For recent reviews, see: (a) Leininger, S.; Olenyuk, B.; Stang, P. J. Chem. Rev. 2000, 100, 853.
2. (b) Swiegers, G. F.; Malefetse, T. J. Chem. Rev. 2000, 100, 3483-3537.
3. (c) Navarro, J. A. R.; Lippert, B. Coord. Chem. Rev. 2001, 222, 219.
4. For comprehensive monographs, see: (a) Transition Metals in Supramolecular Chemistry; Fabrizzi, L., Poggi, A., Eds.; Kluwer Academic Publisher: Dordrecht, The Netherlands, 1994.
5. (b) Transition Metals in Supramolecular Chemistry; Sauvage, J. P., Ed., Wiley: Chichester, U.K., 1999.
6. (c) Comprehensive Supramolecular Chemistry; Lehn, J. M., Chair, Ed.; Atwood, J. L., Davis, J. E. D., McNicol, D. D., Vogtl, F., Executive Eds.; Pergamon: Oxford, U.K., 1996; Vol. 1, p1.
7. For reviews, see: (a) References la-c.
8. (b) Fujita, M. Chem. Soc. Rev. 1998, 27, 417.
9. (b) Stang, P. J.; Olenyuk, B. Acc. Chem. Res. 1997, 30, 502.
10. (c) Fujita, M.; Ogura, K. Bull Chem. Soc. Jpn. 1996, 69, 1471.
11. Kitaura, R.; Fujimoto, K.; Noro, S.-i.; Kondo, M.; Kitagawa, S. Angew. Chem., Int. Ed. 2002, 41, 133.
12. (a) Creutz, C.; Taube, H. J. Am. Chem. Soc. 1973, 95, 1086,
13. (b) Kaim, W.; Klein, A.; Glockle, M. Acc. Chem. Res. 2000, 33, 755.
14. (c) Näther, C.; Jess, I.; Greve, J. Polyhedron 2001, 20, 1017.
15. (d) Weber, A.; Ertel, T. S.; Reinohl, U.; Feth, M.; Bertagnoli, H.; Leuze, M.; Hanack, M. Eur. J. Inorg. Chem. 2001, 679.
16. (e) Comprehensive Supramolecular Chemistry; Sauvage, J. P., Hoseeini, M. W., Eds.; Pergamon: Oxford, U.K., 1996; Vol. 9.
17. (f) Ferigo, M.; Bonhote, P.; Marty, W.; Stoeckli-Evans, H. J. Chem. Soc., Dalton Trans. 1994, 1549.
18. (g) Ito, T.; Hamaguchi, T.; Nagino, H.; Yamaguchi, T.; Kido, H.; Zavarine, I. S.; Richmond, T.; Washington, J.; Kubiak, C. P. J. Am. Chem. Soc. 1999, 121, 4625.
19. (a) See ref 5d.
20. (b) Pohmer. J.; Hanack, M.; Barcina, J. O. J. Mater. Chem. 1996, 6, 957.
21. Geiss, A.; Vahrenkamp, H. Inorg. Chem. 2000, 39, 4029 and references therein.
22. Hanack, M.; Kamenzen, S.; Kamenzen, G.; Subramanian, L. R. Synth. Met. 2000, 110, 93.
23. (a) Baxter, P. N. W. J. Org. Chem. 2000, 65, 1257.
24. (b) Ziessel, R.; Hissler, M.; El-ghazoury, A.; Harriman, A. Coord. Chem. Rev. 1998, 178-180, 1251.
25. Dioxocyclams have been extensively developed by Kimura. For reviews, see: (a) Kimura, E. In Crown Ethers and Analogous Compounds; Hiraoka, M., Ed.; Studies in Organic Chemistry 45; Elsevier: New York, 1992; p 381.
26. (b) Kimura, E. Pure Appl. Chem. 1989, 42, 823.
27. For reviews, see: (a) Lindoy, L. F. Chemistry of Macrocyclic Ligand Complexes; Cambridge University Press: London, 1989.
28. (b) Izatt, R. M.; Pawlak, K.; Bradshaw, J. S.; Bruening, R. L. Chem. Rev. 1995, 95, 2529.
29. (c) Martell, A. E.; Hancock, R. D. Metal Complexes in Aqueous Solutions; Plenum Press: New York, 1996.
30. (a) For a review, see: Denat, F.; Brandes, S.; Guilard, R. Synlett 2000, 561-574.
31. (b) Kurosaki, H.; Bucher, C.; Espinosa, E.; Barbe, J.-M.; Guilard, R. Inorg. Chim Acta 2001, 322, 145.
32. (c) Kurosaki, H.; Yoshida, H.; Fujimoto, A.; Goto, M.; Shionoya, M.; Kimura, E.; Espinosa, E.; Barbe, J.-M.; Guilard, R. J. Chem. Soc., Dalton Trans. 2001, 898-901.
33. (a) Lachkar, M.; Guilard, R.; Atmani, D.; DeCian, A.; Fischer, J.; Weiss, R. Inorg. Chem. 1998, 37, 1575.
34. (b) Brandes, S.; Denat, F.; Lacour, S.; Rabiet, F.; Barbette, F.; Pullumbi, P.; Guilard, R. Eur. J. Org. Chem. 1998, 2349.
35. (c) Brandes, S.; Lacour, S.; Denat, F.; Pullumbi, P.; Guilard, R. J. Chem. Soc., Perkin Trans. 1 1998, 639.
36. (d) Denat, F.; Lacour, S.; Brandes, S.; Guilard, R. Tetrahedron Lett. 1997, 38, 4417.
37. (a) Puntener, K.; Hellman, M. D.; Kuester, E.; Hegedus, L. S. J. Org. Chem. 2000, 65, 8301.
38. (b) Kuester, E.; Hegedus, L. S. Organometallics 1999, 18, 5318.
39. (c) Hsiao, Y.; Hegedus, L. S. J. Org. Chem. 1997, 62, 3586.
40. (d) Dumas, S.; Lastra, E.; Hegedus, L. S. J. Am. Chem. Soc. 1995, 117, 3368.
41. (e) Hegedus, L. S.; Moser, W. H. J. Org. Chem. 1994, 59, 7779.
42. (f) Betschart, C.; Hegedus, L. S. J. Am. Chem. Soc. 1992, 114, 5010.
43. Wynn, T.; Hegedus, L. S. J. Am. Chem. Soc. 2000, 122, 5034.
44. Fagalde, F.; Katz, N. E. Polyhedron 1995, 14, 1213.
45. Bridger, G. J.; Skerlj, R. T.; Padmanabhan, P.; Martellucci, S. A.; Henson, G. W.; Struyf, S.; Witurouw, M.; Schols, D.; DeClercq, E. J. Med. Chem. 1999, 42, 3971.
46. (a) Adachi, K.; Sugiyama, Y.; Kumagai, H.; Inoue, K.; Kitagawa, S.; Kawata, S. Polyhedron 2001, 20, 1411.
47. (b) Darriet, J.; Haddad, M. S.; Duesler, E. N.; Hendrickson, D. N. Inorg. Chem. 1979, 18, 2679.
48. For recent examples, see: (a) Pickardt, J.; Staub, B. Z. Naturforsch., B.; Chem. Sci. 1997, 52, 1456-1460.
49. (b) Dong, Y.-B.; Smith, M. D.; Layland, R. C.; zur Loye, H.-C. Inorg. Chem. 1999, 38, 5027.
50. (c) Kwiatkowski, E.; Romanowski, G.; Nowicki, W.; Suwinska, K. Polyhedron 2001, 20, 1097.
51. Cronin, L.; Mount, A. R.; Parsons, S.; Robertson, N. J. Chem. Soc., Dalton Trans. 1999, 1925.
52. Journaux, Y.; Sletten, J.; Kahn, O. Inorg. Chem. 1986, 25, 439.
53. Goeta, A. E.; Howard, J. A. K.; Maffeo, D.; Puschmann, H.; Williams, J. A.; Gareth, Yufit, D. S. J. Chem. Soc., Dalton Trans. 2000, 1873. Trinuclear copper(II) complexes are also known for their distantly related bis-oximato ligands (Gao, E.-Q.; Zhao, Q.-H.; Tang, D.-Z.; Jiang, Z.-H.; Yan, S.-P. J. Chem. Soc., Dalton Trans. 2001, 1537) and dithiooxamido ligands (Veit, R.; Girerd, J.-J.; Kahn, O.; Robert, F.; Jeannin, Y. Inorg. Chem. 1986, 25, 4175).
54. Goeta, A. E.; Howard, J. A. K.; Maffeo, D.; Puschmann, H.; Williams, J. A.; Gareth, Yufit, D. S. J. Chem. Soc., Dalton Trans. 2000, 1873. Trinuclear copper(II) complexes are also known for their distantly related bis-oximato ligands (Gao, E.-Q.; Zhao, Q.-H.; Tang, D.-Z.; Jiang, Z.-H.; Yan, S.-P. J. Chem. Soc., Dalton Trans. 2001, 1537) and dithiooxamido ligands (Veit, R.; Girerd, J.-J.; Kahn, O.; Robert, F.; Jeannin, Y. Inorg. Chem. 1986, 25, 4175).
55. Goeta, A. E.; Howard, J. A. K.; Maffeo, D.; Puschmann, H.; Williams, J. A.; Gareth, Yufit, D. S. J. Chem. Soc., Dalton Trans. 2000, 1873. Trinuclear copper(II) complexes are also known for their distantly related bis-oximato ligands (Gao, E.-Q.; Zhao, Q.-H.; Tang, D.-Z.; Jiang, Z.-H.; Yan, S.-P. J. Chem. Soc., Dalton Trans. 2001, 1537) and dithiooxamido ligands (Veit, R.; Girerd, J.-J.; Kahn, O.; Robert, F.; Jeannin, Y. Inorg. Chem. 1986, 25, 4175).
56. Koh, Y. B.; Christoph, G. G. Inorg. Chem. 1978, 17, 2590. For Rh(II) dimer bridged pyridyl porphyrins, see: Schaivo, S. L.; Serroni, S.; Puntoriero, F.; Tresoldi, G.; Piraino, P. Eur. J. Inorg. Chem. 2002, 79. For pyrazine-bridged rhodium(II) carboxylates, see: Mori, W.; Hoshino, H.; Nishimoto, Y.; Takamizawa, S. Chem. Lett. 1999, 331.
57. Koh, Y. B.; Christoph, G. G. Inorg. Chem. 1978, 17, 2590. For Rh(II) dimer bridged pyridyl porphyrins, see: Schaivo, S. L.; Serroni, S.; Puntoriero, F.; Tresoldi, G.; Piraino, P. Eur. J. Inorg. Chem. 2002, 79. For pyrazine-bridged rhodium(II) carboxylates, see: Mori, W.; Hoshino, H.; Nishimoto, Y.; Takamizawa, S. Chem. Lett. 1999, 331.
58. Koh, Y. B.; Christoph, G. G. Inorg. Chem. 1978, 17, 2590. For Rh(II) dimer bridged pyridyl porphyrins, see: Schaivo, S. L.; Serroni, S.; Puntoriero, F.; Tresoldi, G.; Piraino, P. Eur. J. Inorg. Chem. 2002, 79. For pyrazine-bridged rhodium(II) carboxylates, see: Mori, W.; Hoshino, H.; Nishimoto, Y.; Takamizawa, S. Chem. Lett. 1999, 331.
59. Rhodium(II) acetate also complexes isonitriles: Eagle, C. T.; Farrar, D. G.; Pfaff, C. U.; Davies, J. A.; Kluwe, C.; Miller, L. Organometallics 1998, 17, 4523. It also complexes nitriles: Miyasaka, H.; Campos-Fernandez, C. S.; Galan-Mascaros, J.; Dunbar, K. R. Inorg. Chem. 2000, 39, 5870.
60. Rhodium(II) acetate also complexes isonitriles: Eagle, C. T.; Farrar, D. G.; Pfaff, C. U.; Davies, J. A.; Kluwe, C.; Miller, L. Organometallics 1998, 17, 4523. It also complexes nitriles: Miyasaka, H.; Campos-Fernandez, C. S.; Galan-Mascaros, J.; Dunbar, K. R. Inorg. Chem. 2000, 39, 5870.
61. (a) Bu, X.-H.; An, D. L.; Chen, Y. T.; Shinoyo, M.; Kimura, E. J. Inclusion Phenom. 1997, 27, 245.
62. This paper reports a red shift from 516 to 576 nm for related pendant quinoline-copper dioxocyclam complexes. See also: (b) Bu, X.-H.; An, D. L.; Cao, X.-C.; Zhang, R. H.; Clifford, T.; Kimura, E. J. Chem. Soc., Dalton Trans. 1998, 2247.
63. (c) Bu, X.-H.; Cao, X.-C.; An, D. L.; Zhang, R. H.; Thomas, C.; Kirnura, E. J. Chem. Soc., Dalton Trans. 1998, 433.
64. Full ESR spectra are contained in the Supporting Information associated with this paper.
65. Drago, R. S. Physical Methods for Chemists, 2nd ed.; Surfside: Gainesville, FL, 1992; p 590. From: Hasty, E. F.; Colburn, T. J.; Hendrickson, D. N. Inorg. Chem. 1973, 12, 2414.
66. Drago, R. S. Physical Methods for Chemists, 2nd ed.; Surfside: Gainesville, FL, 1992; p 590. From: Hasty, E. F.; Colburn, T. J.; Hendrickson, D. N. Inorg. Chem. 1973, 12, 2414.
67. Kimura, E.; Koike, T.; Machida, R.; Nagai, R.; Kodama, M. Inorg. Chem. 1984, 23, 4181.
68. For a detailed discussion of stereoisomerism in capped bis-cyclams, see ref 15.
69. Norman, J. G., Jr.; Kolari, H. J. J. Am. Chem. Soc. 1978, 100, 791.