Shape-persistent phenylene-acetylene macrocycles: Large rings - Low yield?

Angewandte Chemie - International Edition

Volumn 44, Issue 25, 2005, Pages 3806-3808

  Höger, Sigurd ^a  

^a UNIVERSITY OF KARLSRUHE   (Germany)

Author keywords

Alkynes; Cyclophanes; Macrocycles; Metathesis; Supramolecular chemistry

Indexed keywords

AROMATIC COMPOUNDS; MICROSTRUCTURE;

CHEMICAL EQUATION; PHENYLENE-ACETYLENE; PRECURSORS; REVERSIBILITY;

MARINE BIOLOGY;

EID: 21244456892     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200500681     Document Type: Article

References (45)

1. Recent reviews: a) J. S. Moore, Acc. Chem. Res. 1997, 30, 402-413;
2. b) S. Höger, J. Polym. Sci. Part A 1999, 37, 2685-2698;
3. c) M. M. Haley, J. J. Pak, S. C. Brand, Top. Curr. Chem. 1999, 201, 81-130;
4. d) C. Grave, A. D. Schlüter, Eur. J. Org. Chem. 2002, 3075-3098;
5. e) D. Zhao, J. S. Moore, Chem. Commun. 2003, 807-818;
6. f) S. Höger, Chem. Eur. J. 2004, 10, 1320-1329;
7. g) Acetylene Chemistry (Eds.: F. Diederich, P. J. Stang, R. R. Tykwinsky), Wiley-VCH, Weinheim, 2005.
8. a) T. Kawase, H. R. Darabi, M. Oda, Angew. Chem. 1996, 108, 2803-2805;
9. Angew. Chem. Int. Ed. Engl. 1996, 35, 2664-2666;
10. b) T. Kawase, K. Tanaka, N. Shiono, Y. Seirai, N. Shiono, M. Oda, Angew. Chem. 2004, 116, 1754-1756;
11. Angew. Chem. Int. Ed. 2004, 43, 1722-1724.
12. H. A. Staab, K. Neunhoeffer, Synthesis 1974, 424.
13. a) J. S. Moore, J. Zhang, Angew. Chem. 1992, 104, 873-874;
14. Angew. Chem. Int. Ed. Engl. 1992, 31, 922-924;
15. b) J. Zhang, D. J. Pesak, J. L. Ludwick, J. S. Moore, J. Am. Chem. Soc. 1994, 116, 4227-4239.
16. For examples, see: a) H. Staab, F. Binning, Chem. Ber. 1967, 100, 293-305;
17. b) V. Hensel, K. Lützow, J. Jakob, K. Gessler, W. Saenger, A. D. Schlüter, Angew. Chem. 1997, 109, 2768-2770;
18. Angew. Chem. Int. Ed. Engl. 1997, 36, 2654-2656;
19. c) Y. Tobe, N. Utsumi, A. Nagano, K. Naemura, Angew. Chem. 1998, 110, 1347-1349;
20. Angew. Chem. Int. Ed. 1998, 37, 1285-1287.
21. a) H. L. Anderson, J. K. M. Sanders, Angew. Chem. 1990, 102, 1478-1480;
22. Angew. Chem. Int. Ed. Engl. 1990, 29, 1400-1403;
23. b) D. W. J. McCallien, J. K. M. Sanders, J. Am. Chem. Soc. 1995, 117, 6611-6612.
24. a) S. Höger, A.-D. Meckenstock, H. Pellen, J. Org. Chem. 1997, 62, 4556-4557;
25. b) S. Höger, A.-D. Mechenstock, Tetrahedron Lett. 1999, 40, 1735-1736;
26. c) S. Höger, A.-D. Meckenstock, Chem. Eur. J. 1999, 5, 1686-1691;
27. d) S. Höger, Macromol. Symp. 1999, 142, 185-191;
28. e)M. Fischer, S. Höger, Eur. J. Org. Chem. 2003, 441-446.
29. For an example summary, see: S. J. Rowan, S. J. Cantrill, G. R. L. Cousins, J. K. M. Sanders, J. F. Stodart, Angew. Chem. 2002, 114, 938-993;
30. Angew. Chem. Int. Ed. 2002, 41, 898-952.
31. Topical examples of this strategy through self-assembled metalloorganic frameworks: a) M. Fujita, K. Umemoto, M. Yoshizawa, N. Fujita, T. Kusokawa, K. Biradha, Chem. Commun. 2001, 509-518;
32. b) S. R. Seidel, P. J. Stang, Acc. Chem. Res. 2002, 35, 972-983.
33. a) S. Akine, T. Taniguchi, T. Nabeshima, Tetrahedron Lett. 2001, 42, 8861-8864;
34. b) J. Gawronski, H. Kolbon, M. Kwit, A. Katrusiak, J. Org. Chem. 2000, 65, 5768-5773.
35. One of the most impressive recent examples are the Borromean rings of Stoddart: K. S. Chichak, S. J. Cantrill, A. R. Pease, S.-H. Chiu, G. W. V. Cave, J. L. Atwood, J. F. Stoddart, Science 2004, 304, 1308-1312.
36. D. Zhao, J. S. Moore, J. Org. Chem. 2002, 67, 3548-3554.
37. Imine metathesis reactions in various solvents suggest that the formation of stacked-ring assemblies is the thermodynamic driving force for the exclusive formation of cyclodimers: D. Zhao, J. S. Moore, Macromolecules 2003, 36, 2712-2720.
38. A. J. Gallant, M. J. MacLachlan, Angew. Chem. 2003, 115, 5465-5468;
39. Angew. Chem. Int. Ed. 2003, 42, 5307-3310.
40. C. Ma, A. Lo, A. Abdolmaleki, M. J. MacLachlan, Org. Lett. 2004, 6, 3841-3844.
41. W. Zhang, J. S. Moore, J. Am. Chem. Soc. 2004, 126, 12 796.
42. With the "instant catalysts" described by Bunz, the cyclohexamer was obtained in only 6% yield, similar to synthesis of Staab: a) P.-H. Ge, W. Fu, W. A. Herrmann, E. Herdtweck, C. Campana, R. D. Adams, U. H. F. Bunz, Angew. Chem. 2000, 112, 3753-3756;
43. Angew. Chem. Int. Ed. 2000, 39, 3607-3610;
44. b) U. H. F. Bunz, Acc. Chem. Res. 2001, 34, 998-1010.
45. Previous experiments by Moore and co-workers have shown that high conversions in the metathesis reaction could be obtained in a closed system if the reaction product is insoluble in the reaction mixture; W. Zhang, S. Kraft, J. S. Moore, J. Am. Chem. Soc. 2004, 126, 329-335.