Directed synthesis of monofunctionalized 5,5'-disubstituted 2,2'- bipyridines and their first application as metallo-supramolecular initiators

Tetrahedron Letters

Volumn 39, Issue 47, 1998, Pages 8643-8644

  Schubert, Ulrich S ^a   Eschbaumer, Christian ^a   Hochwimmer, Georg ^a  

^a TECHNICAL UNIVERSITY OF MUNICH   (Germany)

Author keywords

Bipyridines; Bromination; Living polymerization; Stille coupling

Indexed keywords

2,2' BIPYRIDINE DERIVATIVE; COPOLYMER; FERROUS ION; IRON COMPLEX; OXAZOLINE DERIVATIVE;

ARTICLE; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0032548038     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)02041-3     Document Type: Article

References (17)

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6. [5] For a recent example see e.g.: Hanan, G. S.; Schubert, U. S.; Volkmer, D.; Riviere, E.; Lehn, J.-M.; Kyritsakas, N.; Fischer, J. Can. J. Chem. 1997, 75, 169-182.
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9. 3, 300 MHz): 2.37 (s, 6 H, 7,7′-H), 7.60 (dd, 2 H, J = 8.0, 2.1, 4,4′-H), 8.24 (d, 2 H, J = 8.0, 3,3′-H), 8.48 (s, 2 H, 6,6′-H).
10. [9] E.g.: Ebmayer, F.; Vögtle, F. Chem. Ber. 1989, 122, 1725-1727.
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13. 3): 7.44 (d, 1 H, J = 8.0, 4′-H), 7.61 (d, 1 H, J = 8.0, 4-H), 8.21 (d, 1 H, J = 5.3, 3′-H), 8.23 (d, 1 H, J = 5.3, 3-H), 8.34 (s, 1 H, 6′-H), 8.48 (s, 1 H, 6-H).
14. [12] See also: Fraser, C. L.; Anastasi, N. R.; Lamba, J. J. S. J. Org. Chem. 1997, 62, 9314-9317.
15. 3): 2.41 (s, 3 H, 7′-H), 4.53 (s, 2 H, 7-H), 7.67 (d, 1 H, J = 8.3, 4′-H), 7.85 (dd, 1 H, J = 8.3, 2.3, 4-H), 8.32 (d, 1 H, J = 7.9, 3′-H), 8.41 (d, 1 H, J = 8.3, 3-H), 8.53 (s, 1 H, 6′-H), 8.67 (s, 1 H, 6-H). Further purification on silica resulting 75% of very pure product (partially destruction on the column).
16. 3CN)/nm (ε): 257 (31 768), 304 (68 293), 525 (3 776).
17. w = 1.32.