Regioselective functionalization of 2,2′-bipyridine and transformations into unsymmetric ligands for coordination chemistry

Acta Chemica Scandinavica

Volumn 52, Issue 1, 1998, Pages 77-85

  Norrby, Thomas ^a   Börje, Anna ^a   Zhang, Lian ^a,b   Åkermark, Björn ^a  

^a ROYAL INSTITUTE OF TECHNOLOGY   (Sweden)

^b Astra Arcus AB   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012095036     PISSN: 0904213X     EISSN: None     Source Type: Journal    
DOI: 10.3891/acta.chem.scand.52-0077     Document Type: Article

References (55)

1. Summers, L. A. Adv. Hetrocycl. Chem. 35 (1984) 281.
2. (a) Barigelletti, F., Flamigni, L., Guardigli, M., Juris, A., Beley, M., Chodorowski-Kimmes, S., Collin, J.-P. and Sauvage, J.-P. Inorg. Chem. 35 (1996) 136;
3. (b) Harriman, A. and Ziessel, R. J. Chem. Soc., Chem. Commun. (1996) 1707;
4. (c) Chodorowski-Kimmes, S., Beley, M., Collin, J.-P. and Sauvage, J.-P. Tet. Lett. 37 (1996) 2963;
5. (d) Coe, B. J., Thompson, D. W., Culbertson, C. T., Schoonover, J. R. and Meyer, T. J. Inorg. Chem. 34 (1995) 3385;
6. (e) Barigelletti, F., Flamigni, L., Balzani, V., Collin, J.-P., Sauvage, J.-P., Sour, A., Constable, E. C. and Cargill Thompson, A. M. W. J. Am. Chem. Soc. 116 (1994) 7692.
7. (a) Barigelletti, F., Flamigni, L., Collin, J-.P. and Sauvage, J.-P. J. Chem. Soc., Chem. Commun. (1997) 333;
8. (b) Balzani, V., Juris, A., Venturi, M., Campagna, S. and Serroni, S. Chem. Rev. 96 (1996) 759;
9. (c) Juris, A., Balzani, V., Barigelletti, F., Campagna, S., Belser, P. and von Zelewsky, A. Coord. Chem. Rev. 84 (1988) 85;
10. (d) Balzani, V. and Scandola, F. Supramolecular Photochemistry, Ellis Horwood, Chichester 1991;
11. (e) Kalyanasundaram, K. Photochemistry of Polypyridine and Porphyrin Complexes, Academic, London 1992;
12. (f) Krause, R. A. Struct. Bonding (Berlin) 67 (1987) 1.
13. (a) Hammarström, L., Alsins, J., Börje, A., Norrby, T., Zhang, L. and Åkermark, B. J. Photochem. Photobiol., A: Chem. 102 (1997) 139;
14. (b) Norrby, T., Börje, A., Åkermark, B., Hammarström, L., Alsins, J., Lashgari, K., Norrestam, R., Mårtensson, J. and Stenhagen, G. Inorg. Chem. Submitted.
15. Sun, L., Hammarström, L., Norrby, T., Davydov, R., Almgren, M., Andersson, M., Berglund, H., Börje, A., Korall, P., Philouze, C., Styring, S. and Åkermark, B. J. Chem. Soc., Chem. Commun. (1997) 607.
16. See, for instance: Barber, J. and Andersson, B. Nature (London) 370 (1994) 31.
17. (a) Della Ciana, L., Hamachi, I. and Meyer, T. J. J. Org. Chem. 54 (1989) 1731;
18. (b) Ghosh, P. K. and Spiro, T. G. J. Am. Chem. Soc. 102 (1980) 5543;
19. (c) Cosnier, S., Deronzier, A. and Moutet, J. C. J. Electroanal. Chem. (1985) 193;
20. (d) Newkome, G. R., Puckett, E. W., Kiefer, G. E., Gupta, V. K., Xia, Y., Coreil, M. and Hackney, M. A. J. Org. Chem. 47 (1982) 4116;
21. (e) Kauffmann, T., Ennen, J., Lhotak, H., Rensing, A., Steinseifer, F. and Woltermann, A. Angew. Chem., Int. Ed. Engl. 19 (1980) 328.
22. (a) Potts, K. T. Bull. Soc. Chim. Belg. 99 (1990) 741;
23. (b) Potts, K. T., Gheysen Raiford, K. A. and Keshavarz-K, M. J. Am. Chem. Soc. 115 (1993) 2793;
24. (c) Potts, K. T. and Winslow, P. A. J. Org. Chem. 50 (1985) 5405;
25. (d) Kröhnke, F. Synthesis (1976) 1;
26. (e) Botteghi, C., Caccia, G., Chelucci, G. and Soccolini, F. J. Org. Chem. 49 (1984) 4290;
27. (f) Weller, D. D., Luellen, G. R. and Weller, D. L. J. Org. Chem. 47 (1982) 4803;
28. (g) Gupta, A. K., Hiriyakkanavar, I. and Hiriyakkanavar, J. Tetrahedron 46 (1990) 2561.
29. (a) Uenishi, J., Tanaka, T., Nishiwaki, K., Wakabayashi, S., Oae, S. and Tsukube, T. J. Org. Chem. 58 (1993) 4382;
30. (b) Undheim, K. and Benneche, T. Heterocycles 30 (1990) 1155;
31. (c) Thompson, W. T., Jones, J. H., Lyle, P. A. and Thies, J. E. J. Org. Chem. 53 (1988) 2052;
32. (d) Rode, T. and Breitmaier, E. Synthesis (1987) 574;
33. (e) Tiecco, M., Testaferri, L., Tingoli, M., Chianelli, D. and Montanucci, M. Synthesis (1984) 736.
34. Wenkert, D. and Woodward, R. B. J. Org. Chem. 48 (1983) 283.
35. (a) Fife, W. K J. Org. Chem. 48 (1983) 1375;
36. (b) Fife, W. K. and Scriven, E. F. V. Heterocycles 22 (1984) 2375.
37. (a) Antonini, I., Claudi, F., Cristalli, G., Franchetti, P., Grifantini, M. and Martelli, S. J. Med. Chem. 24 (1981) 1181;
38. (b) Case, F. H. J. Org. Chem. 31 (1966) 2398.
39. (a) Burstall, F. H. J. Chem. Soc. (1938) 1662;
40. (b) Tsuchia, S. and Seno, M. J. Phys. Chem. 98 (1994) 1682;
41. (c) Parks, J. E., Wagner, B. E. and Holm, R. H. J. Organomet. Chem. 56 (1973), 53.
42. (a) Garelli, N. and Vierling, P. J. Org. Chem. 57 (1992) 3046;
43. (b) Oki, A. R. and Morgan, R. J. Synth. Commun. 25 (1995) 4093.
44. See for instance: Adolfsson, H., Wärnmark, K, and Moberg, C. J. Org. Chem. 59 (1994) 2004.
45. Westheimer, F. H. and Benfey, O. T. J. Am. Chem. Soc. 78 (1956) 5309.
46. Sjögren, M., Hansson, S., Norrby, P.-O., Åkermark, B., Cucciolito, M. E. and Vitagliano, A. Organometallics 11 (1992) 3954.
47. 9a have reported a 60% yield of a crystalline low-melting solid (m.p. 50-51°C) after chromatography on silica gel. We have at one time obtained 14 as a low-melting solid (39-41°C) with the same spectroscopic data as our usual preparations, and of those reported by Kauffmann et al.
48. Breton, P., Andrè-Barrès, C. and Langlois, Y. Synth. Commun. 22 (1992) 2543.
49. Chujo, Y., Sada, K. and Saegusa, T. Polym. J. 6 (1993) 599.
50. Klemm, L. H., Klopfenstein, C. E. and Kelly, H. P. J. Chromatogr. 23 (1966) 428.
51. Meyers, A. I., Temple, D. L., Haidukewych, D. and Mihelich, E. D. J. Org. Chem. 39 (1974) 2787.
52. Tsuchia, S. and Seno, M. J. Phys. Chem. 98 (1994) 1682.
53. Lewis, J. and O'Donoghue, T. D. J. Chem. Soc., Dalton Trans. (1980) 736.
54. Furukawa, N., Takahashi, F., Kawai, T., Kishimoto, K. and Oae, S. Phosphorus Sulfur 16 (1983) 167.
55. Murase, I. Nippon Kagaku Zasshi 77 (1956) 682.