Rearrangement Reactions in Dinuclear Triple Helicates

Inorganic Chemistry

Volumn 36, Issue 23, 1997, Pages 5179-5191

  Meyer, Michel ^a   Kersting, Berthold ^a   Powers, Ryan E ^a   Raymond, Kenneth N ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000027566     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic970864u     Document Type: Article

References (116)

1. Paper no. 4 in the series Coordination Incommensurate Cluster Formartion. For the previous paper see: Caulder, D. L.; Raymond, K. N. Angew. Chem., Int. Ed. Engl. 1997, 36, 1440.
2. Paper no. 4 in the series Coordination Incommensurate Cluster Formartion. For the previous paper see: Caulder, D. L.; Raymond, K. N. Angew. Chem., Int. Ed. Engl. 1997, 36, 1440.
3. (a) Constable, E. C. Tetrahedron 1992, 48, 10013.
4. (b) Lehn, J. M. Supramolecular Chemistry-Concepts and Perspectives; VCH: Weinheim, Germany, 1995.
5. Amabilino, D. B.; Stoddart, J. F. Chem. Rev. 1995, 95, 2725.
6. (a) Chambron, J. C.; Heitz, V.; Sauvage, J. P. J. Am. Chem. Soc. 1993. 115, 12378.
7. (b) Chambron, J. C.; Dietrich-Buchecker, C. O.; Nierengarten, J. F.; Sauvage, J. P.; Solladié, N.; Albrecht-Gary, A. M.; Meyer, M. New J. Chem. 1995, 19, 409.
8. a) Dietrich-Buchecker, C. O.; Sauvage, J. P.; Kern, J. M. J. Am. Chem. Soc. 1984, 106, 3043.
9. (b) Livoreil, A.; Dietrich-Buchecker, C. O.; Sauvage, J. P. J. Am. Chem. Soc. 1994, 116, 9399.
10. Nierengarten, J. F.; Dietrich-Buchecker, C. O.; Sauvage, J. P. New J. Chem. 1996, 20, 685.
11. Fujita, M.; Nagao, S.; Ogura, K. J. Am. Chem. Soc. 1995, 117, 1649.
12. (e) Fujita, M.; Oguro. D.; Miyazawa, M.; Oka, H.; Yamaguchi, K.; Ogura, K. Nature 1995, 378, 6556.
13. (a) Dietrich-Buchecker, C. O.; Sauvage, J. P. New J. Chem. 1992, 16, 277.
14. (b) Dietrich-Buchecker, C. O.; Sauvage, J. P. J. Am. Chem. Soc. 1996, 118, 9110.
15. Leize, E.; Van Dorsselaer, A.; Kramer, R.; Lehn, J. M. J. Chem. Soc., Chem. Commun. 1993, 990.
16. (a) Baxter, P.; Lehn, J. M.; DeCian, A.; Fisher, J. Angew. Chem., Int. Ed. Enal. 1993, 32, 69.
17. (b) Fujita, M.; Ibukuro, F.; Hagihara, H.; Ogura, K. Nature 1994, 367, 720.
18. Marquis-Rigault, A.; Dupont-Gervais, A.; Baxter, P. N. W.; Van Dorsselaer, A.; Lehn, J. M. Inorg. Chem. 1996, 35, 2307.
19. (a) Youinou, M. T.; Rahmouni, N.; Fisher, J.; Osborn, J. A. Angew. Chem., Int. Ed. Engl. 1992, 31, 733.
20. (b) Baxter, P.; Lehn, J. M.; Fisher, J.; Youinou, M. T. Angew. Chem.. Int. Ed. Engl. 1994, 33, 2284.
21. Hanan, G. S.; Arana, C. R.; Lehn, J. M.; Fenske, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1122.
22. (a) Fujita, M.; Yazaki, J.; Ogura, K. J. Am Chem. Soc. 1990, 112, 5645.
23. (b) Drain, C. M.; Lehn, J. M. J. Chem. Soc., Chem. Commun. 1994, 2313.
24. Stang, P. J.; Cao, D. H. J. Am. Chem. Soc. 1994, 116. 4981.
25. Stang, P. J.; Cao, D. H.; Saito, S.; Arif, A. M. J. Am. Chem. Soc. 1995, 117, 6273.
26. (e) Hunter. C. A. Angew. Chem., Int. Ed. Engl. 1995, 34, 1079.
27. (f) Bilyk, A.; Harding, M. M. J. Chem. Soc., Chem. Commun. 1995, 1697.
28. (g) Olenyuk, B.; Whiteford, J. A.; Stang, P. J. J. Am. Chem. Soc. 1996, 118, 8221.
29. (a) Saalfrank, R. W.; Stark, A.; Bremer, M.; Hummel, H. U. Angew. Chem., Int. Ed. Engl. 1990, 29, 311.
30. (b) Saalfrank, R. W.; Hörner, B.; Stalke, D.; Salbeck, J. Angew. Chem., Int. Ed. Engl. 1993, 32, 1179.
31. (cl Saalfrank, R. W.; Burak, R.; Breit, A., Stalke, D.; Herbst-Irmer, R.; Daub, J.; Forsch, M.; Bill, E.; Müther, M.; Trautwein, A. X. Angew. Chem., Int. Ed. Engl. 1994, 33, 1621.
32. Saalfrank, R. W.; Burak, R.; Reihs, S.; Löw, N.; Hampel, F.; Stachel, H. D.; Lentmaier, J.; Peters, K.; Peters, E. M.; von Schnering, H. G. Angew. Chem., Int. Ed. Engl. 1995, 34, 993.
33. (e) Amoroso, A. J.; Jeffery, J. C.; Jones, P. L., McCleverty, J. A.; Thornton, P.; Ward, M. D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1443.
34. (f) Fujita, M.; Oguro, D.; Miyazawa, M.; Oka, H.; Yamaguchi, K.; Ogura, K. Nature 1995, 378, 469.
35. Beissel, T.; Powers, R. E.; Raymond, K. N. Angew. Chem., Int. Ed. Engl. 1996, 35, 1084.
36. Lindsey, J. S. New. Chem. 1991, 15, 153.
37. (a) Struckmeir, G.; Thewalt, U.; Furhop, J. H. J. Am. Chem. Soc. 1976, 98, 278.
38. (b) Lehn, J. M.; Sauvage, J. P.; Simon, J.; Ziessel, R.; Piccini-Leopardi, C.; Germain, G.; Delcercq, J. P.; Van Meerssohe, M. Nouv. J. Chim. 1983, 7, 413.
39. Gisselbrecht, J. P.; Gross, M.; Lehn, J. M.; Sauvage, J. P.; Ziessel, R.; Piccini-Leopardi, C.; Arrieta, J. M.; Germain, G.; Van Meerssche, M. Nouv. J. Chim. 1984, 8, 661.
40. Lehn, J. M.; Rigault, A.; Siegel, J.; Harrowfïeld, J.; Chevrier, B.; Moras, D. Proc. Natl. Acad. Sci. U.S.A. 1987, 84, 2565.
41. (e) Lehn, J. M.; Rigault, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 1095.
42. (f) Koert, U.; Harding, M. M.; Lehn, J. M. Nature 1990, 346, 339.
43. (g) Garret, T. M.; Koert, U.; Lehn, J. M.; Rigault, A.; Meyer, D.; Fisher, J. J. Chem. Soc., Chem. Commun. 1990, 557.
44. (h) Youinou, M. T.; Ziessel, R.; Lehn, J. M. Inorg. Chem. 1991, 30, 2144.
45. Potts, K. T.; Keshavarz-K. M., Tham, F. S.; Abruña, H. D.; Arana, C. R. Inorg. Chem. 1993, 32, 4450.
46. (j) Schoentjes, B.; Lehn, J. M. Helv. Chim. Acta 1995, 78, 1.
47. (k) Woods, C. R.; Benaglia, M.; Cozzi, F.; Siegel, J. S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1830.
48. (a) Carrano, C. J.; Raymond, K. N. J. Am. Chem. Soc. 1978, 100, 5371.
49. (b) Carrano, C. J.; Cooper, S. R.; Raymond, K. N. J. Am. Clem. Soc. 1979, 101, 599.
50. Potts, K. T.; Horwitz, C. P.; Fessak, A.; Keshavarz-K. M.; Nash, K. E.; Toscano, P. J. J. Am. Chem. Soc. 1993, 115, 10444.
51. (a) Potts, K. T.; Keshavarz-K. M.; Tham, F. S.; Abruña, H. D.; Arana, C. R. Inorg. Chem. 1993, 32, 4422.
52. (b) Potts, K. T.; Keshavarz-K, M.; Tham, F. S.; Abruña, H. D.; Arana, C. Inorg. Chem. 1993, 32, 4436.
53. Potts, K. T.; Keshavarz-K, M.; Tham, F. S.; Gheysen Raiford, K. A.; Arana, C.; Abruña, H. D. Inorg. Chem. 1993, 32, 5477.
54. Constable, E. C.; Hannon, M. J.; Tocher, D. A. J. Chem. Soc., Dalton Trans. 1993, 1883.
55. (e) Constable, E. C.; Hannon, M. J.; Edwards, A. J.: Raithby, P. R. J. Chem. Soc., Daltan Trans. 1994, 2669.
56. Piguet, C.; Bernardinelli, G.; Bocquet, B.; Quattropani, A.; Williams, A. F. J. Am. Chem. Soc. 1992, 114, 7440.
57. (a) Scarrow, R. C.; White, D. L.; Raymond, K. N. J. Am. Chem. Soc. 1985, 107, 6540.
58. (b) Williams, A. F.; Piguet, C.; Bernardinelli, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 1490.
59. Piguet, C.; Bernardinelli, G.; Bocquet, B.; Schaad, O.; Williams, A. F. Inorg. Chem. 1994, 33, 4112.
60. Krämer, R.; Lehn, J. M.; De Cian, A.; Fisher, J. Angew. Chem., Int. Ed. Engl. 1993, 34, 582.
61. (e) Zurita, D.; Baret, P.; Pierre, J. L. New J. Chem. 1994, 18, 1143.
62. (a) Libman, J.; Tor, Y.; Shanzer, A. J. Am. Chem. Soc. 1987, 109, 5880.
63. (b) Zelikovich, L.; Libman, J.; Shanzer, A. Nature 1995, 374, 790.
64. (a) Bernardinelli, G.; Piguet, C.; Williams, A. F. Angew. Chem., Int. Ed. Engl. 1992, 31, 1622.
65. (b) Piguet, C.; Bünzli, J. C. G.; Bernardinelli, G.; Hopfgartner, G.; Williams, A. F. J. Am. Chem. Soc. 1993, 115, 8197.
66. Piguet, C.; Bünzli, J. C. G.; Bernardinelli, G.; Bochet, C. G.; Froidevaux, P. J. Chem. Soc., Dalton Trans. 1995, 83,
67. Bünzli, J. C. G.; Froidevaux, P.; Piguet, C. New J. Chem. 1995, 19, 661.
68. Hasenknopf, B.; Lehn, J. M.; Baum, G.; Fenske, D. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 1397.
69. Hasenknopf, B.; Lehn, J. M.; Kneisel, B. O.; Baum, G.; Fenske, D. Angew. Chem., Int. Ed. Engl. 1996, 35, 1838.
70. (a) Piguet, C.; Hopfgartner, G.; Bocquet, B.; Schaad, O.; Williams, A. F. J. Am. Chem. Soc. 1994, 116, 9092.
71. (b) Piguet, C.; Bocquet, B.; Hopfgartner, G. Helv. Chim. Acta 1994, 77, 931.
72. Piguet, C.; Hopfgartner, G.; Williams, A. F.; Bünzli, J. C. G. J. Chem. Soc., Chem. Commun. 1995, 491.
73. Piguet, C.; Rivara-Minten, E.; Hopfgartner, G.; Bünzli, J. C. G. Helv. Chim. Acta 1995, 78, 1541.
74. (e) Piguet, C.; Bernardinelli, G.; Williams, A. F.; Bocquet, B. Angew. Chem., Int. Ed. Engl. 1995, 34, 582.
75. (f) Piguet, C.; Bernardinelli, G.; Bünzli, J. C. G.; Petoud, S.; Hopfgartner, G. J. Chem. Soc., Chem. Commun. 1995, 2575.
76. Fischer, E. Ber. Dtsch. Chem. Ges. 1894, 27, 192.
77. Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 35, 1155.
78. (a) Garrett, T. M.; Koert, U.; Lehn, J. M. J. Phys. Org. Chem. 1992, 5, 529.
79. (b) Pfeil, A.; Lehn, J. M. J. Chem. Soc. Chem. Commun. 1992, 838.
80. Raymond, K. N.; Caulder, D.; Powers, R. E.; Beissel, T.; Meyer, M.; Kersting, B. Coordination Number Incommensurate Cluster Formation. Proc. Robert A. Welch Found. Conf. Chem. Res. 1996, 40, 115.
81. Hou, Z.; Sunderland, C. J.; Nishio, T.; Raymond, K. N. J. Am. Chem. Sac. 1996, 118, 5148.
82. Albrecht, M.; Kotila, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1208.
83. Enemark, E. J.; Stack, T. D. P. Inorg. Chem. 1996, 35, 2719.
84. Kersting, B.; Telford, J. R.; Meyer, M.; Raymond, K. N. J. Am. Chem. Soc. 1996, 118, 5712.
85. (a) Raymond, K. N.; Müller, G.; Matzanke, B. F. Top. Curr. Chem. 1984, 123, 49.
86. (b) Matzanke, B. F.; Müller-Matzanke, G.; Raymond, K. N. Iron Carriers and Iron Proteins. In Physical Bioinorganic Chemistry Series; Loehr, T. M., Ed.; VCH Publishers: New York, 1989, pp 1-121.
87. Teltbrd, J. R.; Raymond, K. N. Siderophores, In Comprehensive Supranmolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Eds.; Elsevier Science Ltd.: Oxford, U.K., 1996; Vol. 1, pp 245-266.
88. (a) Carrano, C. J.; Raymond, K. N. J. Bacterial. 1978, 136, 69.
89. (b) Müller, G.; Barclay, S. J.; Raymond, K. N. J. Biol. Chem. 1985, 260, 13916.
90. Müller, G.; Isowa, Y.; Raymond, K. N. J. Biol. Chem. 1985, 260, 13921
91. The racemization mechanism of a dinuclear cobalt(III) helicate has recently been reported: Charbonnière, L. J.; Gilet, M. F.; Bernauer, K.; Williams, A. F. Chem. Commun. 1996, 39.
92. For a preliminary account on this work, see: Kersting, B.; Meyer. M.; Powers, R. E.; Raymond, K. N. J. Am. Chem. Soc. 1996, 118, 7221.
93. CAChe™ program v. 3.8: Oxford Molecular Group Inc., 1995.
94. Enemark, E. J.; Stack, T. D. P. Angew. Chem., Int. Ed. Engl. 1995, 34, 996.
95. Albrecht, M.; Kotila, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 2134.
96. Albrecht, M.; Franklin, S. J.; Raymond, K. N. Inorg. Chem. 1994, 33, 5785.
97. Karpishin, T. B.; Stack, T. D. P.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 6115.
98. Bradley, D. C.; Holloway, C. E. J. Chem. Soc. A 1969, 282.
99. Fay, R. C.; Lindmark, A. F. J. Am. Chem. Soc. 1975, 97, 5928.
100. (a) Kepert, D. L. Inorganic Stereochemistry, Springer Verlag: Heidelberg, 1982.
101. (b) Borgias, B. A.; Barclay, S. J.; Raymond, K. N. J. Coord. Chem. 1986, 15, 109.
102. Karpishin, T. B.; Stack, T. D. P.; Raymond. K. N. J. Am. Chem. Soc. 1993, 115, 182.
103. Binsch, G.; Kessler, H. Angew. Chem., Int. Ed. Engl. 1980, 19, 411.
104. These data may be found in the Supporting Information.
105. Wilkins, R. G. The Study of Kinetics and Mechanism of Reactions of Transition Metal Complexes, Allyn and Bacon, Inc.; Boston, MA, 1974.
106. Abbreviations: acac, 2,4-pentadione; DCC, 1,3-dicyclohexylcarbodiimide; DCU, 1,3-dicyclohexylurea; DMAP, 4-dimethylaminopyridine; NBA, nitrobenzyl alcohol; TGG. thioglycerol/glycerol.
107. Weitl, F. L.; Raymond, K. N.; Durbin, P. W. J. Med. Chem. 1981, 24, 203.
108. Hou, Z.; Whisenhunt, D. W.; Xu, J.; Raymond, K. N. J. Am. Chem. Soc. 1994, 116, 840.
109. SMART, Area-Detector Software Package; Siemens Industrial Automation, Inc.: Madison, WI, 1993.
110. SAINT, SAX Area-Detector Integration Program v. 4.024; Siemens Industrial Automation, Inc.: Madison, WI, 1995.
111. SHELXTL, Crystal Structure Determination Package: Siemens Industrial Automation, Inc.: Madison, WI, 1994.
112. Martell, A. E.; Motekaitis, R. M. Determination and Use of Stability Constants; VCH: New York, 1988.
113. Perrin, D. D.; Dempsey, B. Buffers for pH and Metal Ion Control; Chapman and Hall Ltd: London. 1974.
114. Jackman, L. M.; Cotton, F. A. Dynamic Nuclear Magnetic Resonance Spectroscope; Academic Press: New York, 1975.
115. (a) Kleier, D. A.; Binsch, G. QCPE No. 165.
116. (b) Bushweller, C. A.; Bhat, G.; Lelandre, L. J.; Brunelle, T. A.; Bilofsky, H. S.; Ruben, H.; Templeton, D. A.; Zalkin, A. J. Am. Chem. Soc. 1975, 97, 65. DNMR3 is part of The University of Manitoba NMR Spectral Simulation and Analysis Package. X-11/Motif Version 940101.