A new generation of 6,6′-disubstituted 2,2′-bipyridines: Towards novel oligo(bipyridine) building blocks for potential applications in materials science and supramolecular chemistry

European Journal of Organic Chemistry

Volumn , Issue 11, 1998, Pages 2573-2581

  Schubert, Ulrich S ^a   Kersten, Jörg L ^b   Pemp, Alexander E ^c   Eisenbach, Claus D ^b   Newkome, George R ^d  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

^b UNIVERSITY OF STUTTGART   (Germany)

^c UNIVERSITY OF BAYREUTH   (Germany)

^d UNIVERSITY OF SOUTH FLORIDA   (United States)

Author keywords

Functionalized bipyridines; Oligo(bipyridines); Supramolecular chemistry

Indexed keywords

EID: 0002646961     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199811)1998:11<2573::AID-EJOC2573>3.0.CO;2-I     Document Type: Article

References (109)

1. [1a] J.-M. Lehn, Angew. Chem. 1990, 102, 1347-1362; Angew. Chem. Int. Ed. Eng. 1990, 29, 1304-1319.
2. [1a] J.-M. Lehn, Angew. Chem. 1990, 102, 1347-1362; Angew. Chem. Int. Ed. Eng. 1990, 29, 1304-1319.
3. [1b] J.-M. Lehn, Supramolecular Chemistry - Concepts and Perspectives, VCH, Weinheim, Germany, 1995.
4. [1c] G. M. Whitesides, J. P. Mathias, C. T. Seto, Science 1991, 254, 1312-1319.
5. [1d] D. S. Lawrence, T. Jiang, M. Levett, Chem. Rev. 1995, 95, 2229-2260.
6. [1e] J.-M. Lehn, Science 1993, 260, 1762-1763.
7. [2a] J. M. Thomas, Angew Chem. 1994, 106, 963-989; Angew. Chem. Int. Ed. Eng. 1994, 33, 913-937.
8. [2a] J. M. Thomas, Angew Chem. 1994, 106, 963-989; Angew. Chem. Int. Ed. Eng. 1994, 33, 913-937.
9. [2b] E. Monflier, E. Blouet, Y. Barnaux, A. Mortreux, Angew. Chem. 1994, 106, 2183-2785; Angew. Chem. Int. Ed. Eng. 1994, 33, 2100-2102.
10. [2b] E. Monflier, E. Blouet, Y. Barnaux, A. Mortreux, Angew. Chem. 1994, 106, 2183-2785; Angew. Chem. Int. Ed. Eng. 1994, 33, 2100-2102.
11. [2c] W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588-1609; Angew. Chem. Int. Ed. Eng. 1993, 32, 1524-1544.
12. [2c] W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588-1609; Angew. Chem. Int. Ed. Eng. 1993, 32, 1524-1544.
13. [3a] P. L. Boulas, M. Gómez-Kaifer, L. Echegoyen, Angew. Chem. 1998, 110, 226-258; Angew. Chem. Int. Ed. Engl. 1998, 37, 216-247.
14. [3a] P. L. Boulas, M. Gómez-Kaifer, L. Echegoyen, Angew. Chem. 1998, 110, 226-258; Angew. Chem. Int. Ed. Engl. 1998, 37, 216-247.
15. [3b] H. Sleiman, P. Baxter, J.-M. Lehn, K. Rissanen, J. Chem. Soc., Chem. Commun. 1995, 715-716.
16. [3c] G. S. Hanan, C. R. Arana, J.-M. Lehn. D. Fenske, Angew. Chem. 1995, 107, 1191-1193: Angew Chem. Int. Ed. Engl. 1995, 34, 1122-1124.
17. [3c] G. S. Hanan, C. R. Arana, J.-M. Lehn. D. Fenske, Angew. Chem. 1995, 107, 1191-1193: Angew Chem. Int. Ed. Engl. 1995, 34, 1122-1124.
18. [3d] K. T. Potts, M. Keshavarz-K, F. S. Tham, H. D. Abruña, C. R. Arana, Inorg. Chem. 1993, 32, 4422-4435.
19. [3e] E. C. Constable, M. J. Hannon, D. A. Tochter, J. Chem. Soc., Dalton Trans. 1993, 1883-1890.
20. [4a] V. Balzani, F. Scandola in Supramolecular Photochemistry (Eds.: E. Horwood), Chichester, 1991.
21. [4b] L. Fabbrizzi, M. Licchelli, P. Pallavivini, A. Perotti, D. Sacchi, Angew. Chem. 1994, 106, 2051-2053; Angew. Chem. Int. Ed. Eng. 1994, 33, 1975-1977.
22. [4b] L. Fabbrizzi, M. Licchelli, P. Pallavivini, A. Perotti, D. Sacchi, Angew. Chem. 1994, 106, 2051-2053; Angew. Chem. Int. Ed. Eng. 1994, 33, 1975-1977.
23. [5a] J.-M. Lehn. Macromol. Symp. 1993, 69, 1-17.
24. [5b] U. S. Schubert, J.-M. Lehn, J. Hassmann, C. Y. Hahn, N. Hallschmidt, P. Müller, in Functional Polymers (Eds.: A. O. Patil, D. N. Schulz, B. M. Novak), ACS Symp. Ser. 1998, 704, 248-260.
25. [6a] J. P. Gisselbrecht, M. Grosse, J.-M. Lehn, J.-P. Sauvage, R. Ziessel. C. Piccini-Leopardi, J. M. Arrieta, G. Germain, M. Van Meersche, Nouv. J. Chim. 1984, 8, 661-667.
26. [6b] J.-M. Lehn, A. Rigault, J. Siegel, J. Harrowfield, B. Chevrier, D. Moras, Proc. Natl. Acad. Sci. USA 1987, 84, 2565-2569.
27. [6c] J.-M. Lehn, A. Rigault, Angew. Chem. 1988, 100, 1121-1122; Angew. Chem. Int. Ed. Eng. 1988, 27, 1095-1097.
28. [6c] J.-M. Lehn, A. Rigault, Angew. Chem. 1988, 100, 1121-1122; Angew. Chem. Int. Ed. Eng. 1988, 27, 1095-1097.
29. [6d] T. M. Garrett, U. Koert, J.-M. Lehn, A. Rigault, D. Meyer, J. Fischer, J. Chem. Soc, Chem. Commun. 1990, 557-558.
30. [6e] U. Koert. M. M. Harding, J.-M. Lehn, Nature 1990, 346, 339-342.
31. [6f] M. M. Harding, U. Koert, J.-M. Lehn, A. Marquis-Rigault, C. Piquet, J. Siegel, Helv. Chim. Acta 1991, 74, 592-610.
32. [6g] R. Krämer, J.-M. Lehn. A. Marquis-Rigault, Proc. Natl Acad. Sci USA 1993, 90, 5394-5398.
33. [6h] E. C. Constable, Prog. Inorg. Chem. 1994, 42, 67-138.
34. [6i] C. O. Dietrich-Buchecker, J.-P. Sauvage. A. DeCian, J. Fischer. J. Chem. Soc., Chem Commun. 1994, 2231-2232.
35. [6j] J.-M. Lehn, J.-B. Regnouf de Vains, Helv. Chim. Acta 1992, 75, 1221-1236.
36. [6k] A. Pfeil, J.-M. Lehn, J. Chem Soc., Chem Commun. 1992, 838-840.
37. [7d] A. Klug, Angew. Chem. 1983, 95, 579-596, Angew Chem. Int. Ed Engl. 1983, 22, 565-582.
38. [7d] A. Klug, Angew. Chem. 1983, 95, 579-596, Angew Chem. Int. Ed Engl. 1983, 22, 565-582.
39. [7d] A. Klug, Angew. Chem. 1983, 95, 579-596, Angew Chem. Int. Ed Engl. 1983, 22, 565-582.
40. [7d] A. Klug, Angew. Chem. 1983, 95, 579-596, Angew Chem. Int. Ed Engl. 1983, 22, 565-582.
41. [7d] A. Klug, Angew. Chem. 1983, 95, 579-596, Angew Chem. Int. Ed Engl. 1983, 22, 565-582.
42. C. R. Woods, M. Benaglia, F Cozzi, J. J. Siegel, Angew. Chem. 1996, 108, 1977-1980; Angew. Chem. Int. Ed. Eng. 1996, 35, 1830-1833.
43. C. R. Woods, M. Benaglia, F Cozzi, J. J. Siegel, Angew. Chem. 1996, 108, 1977-1980; Angew. Chem. Int. Ed. Eng. 1996, 35, 1830-1833.
44. [9a] C. D. Eisenbach, U. S. Schubert, Macromolecules 1993, 26, 7372-7374.
45. [9b] C. D. Eisenbach, U. S. Schubert, G. R. Baker, G. R. Newkome. J. Chem. Soc., Chem. Commun. 1995, 69-70.
46. [9c] M. Antonietti, S. Lohmann, C. D. Eisenbach, U. S. Schubert, Macromol Rapid Commun. 1995, 16, 283-289.
47. [9d] C. D. Eisenbach, A. Göldel, H. Hayen, T. Heinemann, U. S. Schubert, M. Terskan-Reinold in Macromolecular Engineering: Contemporary Themes (Eds.: M. Mishra, S. Kobayashi, O. Nuyken, Y. Yagei, B. Sar), Plenum Publ. Corp., New York, 1995, 207-218.
48. [9e] C. D. Eisenbach, A. Göldel, M. Terskan-Reinold, U. S. Schubert in Polymeric Materials Encyclopedia (Eds.: J. C. Salamone), CRC Press, Boca Raton. 1996, 8162-8172.
49. [9f] C. D. Eisenbach, W. Degelmann, A. Göldel, J. Heinlein, M. Terskan-Reinold, U. S. Schubert, Macromol. Symp. 1995, 98, 565-572.
50. [9g] C D. Eisenbach, A. Göldel, M. Terskan-Reinold, U. S. Schubert, Makromol. Chem, Phys. 1995, 196, 1077-1091.
51. [9h] A. Göldel. U. S. Schubert, C. D. Eisenbach, J. Microscopy 1997, 186, 67-74.
52. [10a] S. Tamagaki, R. J. Card, D. C. Neckers, J. Am. Chem Soc. 1978, 100, 6635-6639.
53. [10b] G. R. Newkome, A. Yoneda, Macromol Chem., Rapid Commun. 1983, 4, 575-581.
54. [10c] Y.-P. Wang, D. C Neckers, Reactive Polymers 1985, 3, 181-189.
55. [10d] T. Maruyama, K. Kubota, T. Yamamoto, Macromolecules 1993, 26, 4055-4057.
56. [10e] G. Hochwimmer, O. Nuyken, U. S. Schubert, Macromol. Rapid Commun. 1998, 19, 309-313.
57. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
58. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
59. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
60. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
61. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
62. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
63. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
64. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
65. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
66. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
67. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
68. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
69. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
70. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
71. [11o] A. Bilyk, M. M. Harding, J. Chem. Soc., Dalton Trans. 1994, 77-82.
72. [12a] G. R. Newkome, W. E. Puckett G. E. Kiefer, V. K. Gupta, Y.-J. Xia, M. Coreil, M. A. Hackney, J Org. Chem. 1982, 47, 4116-4120.
73. [12b] G. R. Newkome, D. C. Pantaleo, W. E. Puckett, P. L. Ziefle, W. A. Deutsch, Inorg. Nucl. Chem. 1981, 43, 1529-1531.
74. [12c] G. R. Newkome, G. E. Kiefer, N. Matsumura, W. E. Puckett, J. Org. Chem. 1985, 50, 3807-3810.
75. [12d] G. R. Newkome, G. E. Kiefer, Y.-J. Xia. V. K. Gupta, Synthesis 1984, 676-679.
76. [12e] G. R. Newkome, D. C. Hager, J. Am. Chem. Soc. 1978, 100, 5567-5568.
77. [12f] G. R. Newkome, D. K. Kohli, F. R. Fronczek. J. Chem. Soc., Chem Commun 1980, 9-11.
78. [12g] G. R. Newkome, D. K. Kohh, Heterocvdes 1981, 75, 739-742.
79. [12h] G. R. Newkome, S. Pappalardo, V. K. Gupta, F. R Fronczek, J. Org. Chem. 1983, 48, 4848-4851.
80. [12i] G. R. Newkome, V. K. Gupta, F. R. Fronczek, S. Pappalardo, Inorg. Chem. 1984, 23, 2400-2408.
81. [12j] G. R. Newkome, V. K. Gupta, F. R. Fronczek, Inorg. Chem. 1983, 22, 171-174.
82. [12k] R Newkome, G. E. Kiefer, W E. Puckett, T. Vreeland, J. Org. Chem. 1983, 48, 5112-5114.
83. [13a] G. R. Newkome, H. W. Lee, J. Am. Chem. Soc. 1983, 105, 5956-5957.
84. [13b] J. L. Toner, Tetrahedron Lett. 1983, 24, 2707-2710.
85. I. Antonini, F. Claudi, G. Cristalli, P. Franchetti, M. Grifantini, S. Martelli, J. Med. Chem. 1981, 24, 1181-1184.
86. See e.g.. V.-M. Mukkala, M. Helenius, I. Hemmilä. J. Kankara, H. Takalo, Helv. Chim Acta 1993, 76, 1361-1378.
87. G. R. Newkome, G. E. Kiefer, D. K. Kohli, Y-J. Xia, F. R. Fronczek, G. R. Baker. J. Org. Chem. 1989, 54, 5105-5110.
88. First observed: H. W. Lee, Dissertation, Louisiana State University, 1983.
89. All efforts to let bisfunctionalized compounds like the bis(bromomethyl)-substituted bipyridine react with 1 equivalent of an appropriate alcoholate resulted in a mixture of bisreacted product and starting material: U. S. Schubert, M. Terskan-Reinold, C. D. Eisenbach, unpublished results - M. Terskan-Reinoid, Dissertation, Universität Bayreuth, 1995.
90. All efforts to let bisfunctionalized compounds like the bis(bromomethyl)-substituted bipyridine react with 1 equivalent of an appropriate alcoholate resulted in a mixture of bisreacted product and starting material: U. S. Schubert, M. Terskan-Reinold, C. D. Eisenbach, unpublished results - M. Terskan-Reinoid, Dissertation, Universität Bayreuth, 1995.
91. G. R. Newkome, J. Groß, A. K. Patri, J. Org. Chem. 1997, 62, 3013-3014
92. [16].
93. [21a] A. J. Mancuso, S.-L. Huang, D. Swern, J. Org. Chem. 1978, 43, 2480-2482.
94. [21b] A. J. Mancuso, S.-L. Huang, D. Swern, Synthesis 1981, 165-185.
95. [21c] W. Carruthers, Some Modern Methods of Organic Synthesis, Cambride University Press, Cambridge, UK, 1987.
96. See e.g.: F. J. Hoogesteger, L. W. Jenneskens, H. Kooijman, N. Veldman, A. L. Spek, Tetrahedron 1996, 52, 1773-1784.
97. In the presence of wet air and heat 6-(methylsulfonyloxymethyl)-6′-(hydroxymethyl)-2,2′-bipyridine (3) gave 6.6′-bis(methylsulfonyloxymethyl)-2,2′-bipyridine and 6.6′-bis(hydroxymethyl)-2,2′-bipyridine (1).
98. [9f][9g].
99. Isolation using kugelrohr distillation to remove the excess of the butane spacer.
100. [26a] C. D. Eisenbach, H. Nefzger in Multiphase Macromolecular Systems, Contemporary Topics in Polymer Sci. (Ed. W. M. Culbertson), Plenum, New York, 1989, 6, pp. 339.
101. [26b] C. D. Eisenbach, E. Stadler, Makromol. Chem. Phvs. 1995, 196, 833-856.
102. [27a] P. Schultheiss-Reimann, H. Kunz, Angew. Chem. 1983, 95, 64-64; Angew. Chem. Int. Ed. Eng. 1983, 22, 62-63.
103. [27a] P. Schultheiss-Reimann, H. Kunz, Angew. Chem. 1983, 95, 64-64; Angew. Chem. Int. Ed. Eng. 1983, 22, 62-63.
104. [27b] N. Kunesch, C. Miet, J. Poisson, Tetrahedron Lett. 1987, 28, 3569-3572.
105. [28a] E. C. Corey. J.-L. Gras, P. Ulrich, Tetrahedron Lett. 1976, 809-812.
106. [28b] P. J. Kocienski, Protecting Groups, Thieme, Stuttgart, Germany, 1994, 68-71.
107. [29a] J.-C. Rodriguez-Ubis, B. Alpha, D. Plancherel, J.-M. Lehn. Helv. Chim Acta 1984, 67, 2264-2269.
108. [29b] H. Dürr, K. Zengerle, H.-P. Trierweiler, Z. Naturforschung, 1988, 43, 361-367.
109. The excess 6.6′-dibromomethyl-2,2′-biypridine (21) can be recycled.