A facile synthesis of large extraannular-functionalized phenyl-ethynyl macrocycles containing m-terphenyl units

Organic Letters

Volumn 4, Issue 24, 2002, Pages 4269-4272

  Höger, Sigurd ^a,b   Rosselli, Silvia ^a   Ramminger, Anne Désirée ^a   Enkelmann, Volker ^a  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 19044373206     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol026870y     Document Type: Article

References (25)

1. Reviews about shape-persistent macrocycles: (a) Moore, J. S. Acc. Chem. Res. 1997, 30, 402.
2. (b) Höger, S. J. Polym. Sci., Part A 1999, 37, 2685.
3. (c) Haley, M. M.; Pak, J. J.; Brand, S. C. Topic Curr. Chem. 1999, 201, 81.
4. (d) Grave, C.; Schlüter, A. D. Eur. J. Org. Chem. 2002, 3075.
5. Höger, S.; Meckenstock, A.-D.; Müller, S. Chem. Eur. J. 1998, 4, 2421.
6. (a) Okuyama, K.; Hasegawa, T.; Ito, M.; Mikami, N. J. Phys. Chem. 1984, 88, 1711.
7. (b) Höger, S.; Enkelman, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 2713.
8. (c) Morrison, D. L.; Höger, S. J. Chem. Soc. Chem. Commun. 1996, 2313.
9. (d) Höger, S.; Enkelmann, V.; Bonrad, K.; Tschierske, C. Angew. Chem., Int. Ed. 2000, 39, 2268.
10. (e) Höger, S.; Morrison, D. L.; Enkelmann, V. J. Am. Chem. Soc. 2002, 124, 6734.
11. Efficient and simple routes to m-terphenyls were reported by Hart et al.: (a) Du, C.-J. F.; Hart, H.; Ng, K.-K. D. J. Org. Chem. 1986, 51, 3162.
12. (b) Saednya, A.; Hart, H. Synthesis 1996, 1455. However, that approach has limitations with respect to 4,4″-dihalogenated compounds.
13. For an oligo(het)arylene building block in macrocycle synthesis, see, for example: Manickam, G.; Schlüter, A. D. Eur. J. Org. Chem. 2000, 3475.
14. Zimmermann, T.; Fischer, G. W. J. Prakt. Chem. 1987, 329, 975. See also: Dimroth, K.; Neubauer, G. Chem. Ber. 1959, 92, 2042.
15. Zimmermann, T.; Fischer, G. W. J. Prakt. Chem. 1987, 329, 975. See also: Dimroth, K.; Neubauer, G. Chem. Ber. 1959, 92, 2042.
16. Manickam, G.; Schlüter, A. D. Eur. J. Org. Chem. 2000, 3475.
17. Moore, J. S.; Weinstein, E. J.; Wu, Z. Tetrahedron Lett. 1991, 32, 2465.
18. Balaban, A. T.; Dinculescu, A.; Dorofeenko, G. N.; Fischer, G. W. Koblik, A. V.; Mezheritskii, V. V.; Schroth, W. Adv. Heterocycl. Chem., Supp. 2; Academic Press: New York, 1982.
19. For the concept of intraannular functional groups, see, for example: (a) Vögtle, F.; Neumann, P. Tetrahedron 1970, 26, 5299.
20. (b) Weber, E.; Vögtle, F. Chem. Ber. 1976, 109, 1803.
21. (a) Rosselli, S.; Ramminger, A.-D.; Wagner, T.; Silier, B.; Wiegand, S.; Häussler, W.; Lieser, G.; Scheumann, V., Höger, S. Angew. Chem., Int. Ed. 2001, 40, 3138.
22. (b) Höger, S.; Bonrad, K.; Rosselli, S.; Ramminger, A.-D.; Wagner, T.; Silier, B.; Wiegand, S.; Häussler, W.; Lieser, G.; Scheumann, V. Makromol. Symp. 2002, 177, 185.
23. (c) Höger, S. Bonrad, K.; Mourran, A.; Beginn, U.; Möller, M. J. Am. Chem. Soc. 2001, 123, 5651.
24. 4 led to an undefined product mixture.
25. w = 0.0527, GOF = 0.857.