Molecular ribbons containing pyridine rings

Liebigs Annales

Volumn , Issue 12, 1996, Pages 2115-2121

  Breidenbach, Stefan ^a   Ohren, Stefan ^a   Herbst Irmer, Regine ^b   Kotila, Sirpa ^c   Nieger, Martin ^a   Vögtle, Fritz ^a  

^a UNIVERSITY OF BONN   (Germany)

^b Inst fur Anorganische Chemie   (Germany)

^c UNIVERSITY OF JYVÄSKYLÄ   (Finland)

Author keywords

Cyclophanes; Macrocycles; Phanes; Pyridinophanes; Ring compounds

Indexed keywords

EID: 0343228585     PISSN: 09473440     EISSN: None     Source Type: Journal    
DOI: 10.1002/jlac.199619961225     Document Type: Article

References (26)

1. [1a] Review: A. Schröder, H.-B. Mekelburger, F. Vögtle, Top. Curr. Chem. 1994, 172, 179-201.
2. [1b] S. Breidenbach, S. Ohren, M. Nieger, F. Vögtle, J. Chem. Soc., Chem. Commun. 1995, 1237-1238 and references therein;
3. see also [1c] L. F. Lindoy, Nature (London) 1995, 376, 293-294.
4. R. Jaenicke, GDCh-lecture, Bonn, June 1996.
5. S. Breidenbach, S. Ohren, F. Vögtle, Chem. Eur. J. 1996, 2, 832-837.
6. The number of core arene building blocks (pyridine and benzene rings) is called "layer number" (in German: Lagigkeit) and is depicted in angular brackets 〈 〉. The body of a ribbon-shaped molecule that is built up of e.g. three benzene rings is therefore called a benzeno〈3〉phane. On the use of angular brackets see G. Hohner, F. Vögtle. Chem. Ber. 1977, 110, 3052-3077.
7. [5a] W. Josten, D. Karbach, M. Nieger, F. Vögtle, K. Hägele, M. Svoboda, M. Przybylski, Chem. Ber. 1994, 127, 767-777.
8. [5b] W. Josten, S. Neumann, M. Nieger, F. Vögtle, K. Hägele, M. Przybylski, F. Beer, K. Müllen, Chem. Ber. 1994, 127, 2089-2096.
9. S. Breidenbach, S. Ohren, M. Nieger, F. Vögtle, J. Chem. Soc., Chem. Commun. 1995, 1237-1238.
10. A. Schröder, D. Karbach, R. Güther, F. Vögtle, Chem. Ber. 1992, 125, 1881-1887.
11. A. Hantzsch, Justus Liebigs Ann. Chem. 1882, 215, 1-82.
12. First preparation: F. Engelman, Justus Liebigs Ann. Chem. 1886, 231, 37-71.
13. [10a] H. Meyer, H. Tropsch, Monatsh. Chem. 1914, 35, 207-217.
14. [10b] A. Singer, S. M. McElvain in Org. Synth., Coll. Vol. II (Ed.: A. H. Blatt), 6th ed., Wiley, New York, 1950, 214-216.
15. Review on side-chain halogenation in methyl pyridines: W. Mathes, H. Schüly, Angew. Chem. 1963, 75, 235-240.
16. First preparation: P. Griess, G. Harrow, Ber. Dtsch. Chem. Ges. 1888, 21, 2740-2743.
17. For "modern" methods of this oxidation see e.g.: J.-J. Van den Eynde, Tetrahedron 1992, 48, 463-468, and references therein.
18. About the use of NBS see e.g.: [14a] Review: L. Horner, E. H. Winkelmann, Angew. Chem. 1959, 71, 349-365.
19. [14b] W. Offermann, F. Vögtle, Angew. Chem. 1980, 92, 471-472.
20. [14c] S. Futamura, Z.-M. Zong, Bull. Chem. Soc. Jpn. 1992, 65, 345-348, and references therein.
21. K. Ziegler, A. Späth, E. Schaaf, W. Schumann, E. Winkelmann, Justus Liebigs Ann. Chem. 1942, 551, 80-119.
22. 3 are very sparingly soluble in benzene/ethanol, resulting in a stationary equilibrium with a constant concentration that likens dilution conditions. See also: P. Knops, N. Sendhoff, H.-B. Mekelburger, F. Vögtle, Top. Curr. Chem. 1991, 161, 1-36.
23. Compare azabenzeno〈3〉phanes with three benzene rings that are analogues of 9 and 10; see ref. 5a.
24. For host/guest complexes in the solid state see e.g.: K. Endo, T. Sawaki, M. Koyanagi, K. Kobayashi, H. Mashuda, Y. Aoyama, J. Am. Chem. Soc. 1995, 117, 8341-8352, and references therein.
25. G. M. Sheldrick, SHELXTL-Plus, Siemens Analytical X-ray Instruments Inc., Madison, Wi, USA, 1989.
26. G. M. Sheldrick, SHELXL-93, University of Göttingen, 1993.