Novel furan-, thiophene- and benzo[b]thiophene bridged macrocycles of 4,4'-bipyridine

Tetrahedron

Volumn 55, Issue 15, 1999, Pages 4709-4720

  Scheytza, Holger ^a   Reissig, Hans Ulrich ^a   Rademacher, Otto ^a  

^a DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

4,4' Bipyridine; Benzo b thiophene; Furan; Macrocycles; Thiophene

Indexed keywords

4,4' BIPYRIDINE; [2,2] 2,5 FURANOPHANE; BENZOTHIOPHENE; FURAN DERIVATIVE; MACROCYCLIC COMPOUND; THIOPHENE DERIVATIVE; THIOPHENOPHANE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHROMATOGRAPHY; CRYSTAL STRUCTURE; CYCLIZATION; ELECTROCHEMICAL ANALYSIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; SPECTROSCOPY; SYNTHESIS;

EID: 0033537876     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00144-1     Document Type: Article

References (49)

1. H. Scheytza, Dissertation, Technische Universität Dresden, 1998.
2. Some examples were given in: a) P. R. Ashton, B. Odell, M. V. Reddington, A. M. Z. Slawin, J. F. Stoddart, D. J. Williams, Angew. Chem. 1988, 100, 1611; Angew. Chem. Int. Ed. Engl. 1988, 27, 1550;
3. Some examples were given in: a) P. R. Ashton, B. Odell, M. V. Reddington, A. M. Z. Slawin, J. F. Stoddart, D. J. Williams, Angew. Chem. 1988, 100, 1611; Angew. Chem. Int. Ed. Engl. 1988, 27, 1550;
4. b) D. Philp, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, D. J. Williams, J. Chem. Soc., Chem. Commun. 1991, 1584;
5. c) A. C. Benniston, A. Harriman, D. Philp, J. F. Stoddart, J. Am. Chem. Soc. 1993, 115, 5298;
6. d) S. A. Staley, B. D. Smith, Tetrahedron Lett. 1996, 37, 283;
7. e) M. A. Lipton, Tetrahedron Lett. 1996, 37, 287;
8. f) W. Devonport, M. A. Blower, M. R. Bryce, L. M. Goldenberg, J. Org. Chem. 1997, 62, 885.
9. Some examples were reported in: a) P. Neta, M.-C. Richoux, A. Harriman, J. Chem. Soc., Faraday Trans. 2 1985, 81, 1427;
10. b) O. Enea, Electrochimica Acta 1986, 31, 789;
11. c) P. Crouigneau, O. Enea, B. Beden, J. Electroanal. Chem. 1987, 218, 307;
12. d) R. J. Fonseca, J. T. Colina, D. K. Smith, J. Electroanal. Chem. 1992, 340, 341;
13. e) P. L. Anelli, P. R. Ashton, R. Ballardini, V. Balzani, M. Delgado, M. T. Gandolfi, T. T. Goodnow, A. E. Kaifer, D. Philp, M. Pietraszkewicz, L. Prodi, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent, D. J. Williams, J. Am. Chem. Soc. 1992, 114, 193;
14. f) E. A. Smith, R. L. Lilienthal, R. J. Fonseca, D. K. Smith, Anal. Chem. 1994, 66, 3013.
15. a) X. Marguerettaz, R. O'Neill, D. Fitzmaurice, J. Am. Chem. Soc. 1994, 116, 2629;
16. b) X. Marguerettaz, D. Fitzmaurice, J. Am. Chem. Soc. 1994, 116, 5017;
17. c) M. Seiler, H. Dürr, I. Willner, A. Doron, J. F. Stoddart, J. Am. Chem. Soc. 1994, 116, 3399;
18. d) M. Seiler, H. Dürr, Liebigs Ann. Chem. 1995, 407;
19. e) L. N. Cusack, S. N. Rao, D. Fitzmaurice, Chem. Eur. J. 1997, 3, 202.
20. D. B. Amabilino, J. F. Stoddart, Chem. Rev. 1995, 95, 2725.
21. For recent examples see: a) P. R. Ashton, I. Iriepa, M. V. Reddington, N. Spencer, A. M. Z. Slawin, J. F. Stoddart, D. J. Williams, Tetrahedron Lett. 1994, 35, 4835;
22. b) N. Deng, V. R. Marhawa, M. E. Garcia, A. Benesi, T. E. Mallouk, Tetrahedron Lett. 1995, 36, 7599;
23. c) M. Asakawa, C. L. Brown, D. Pasini, J. F. Stoddart, P. G. Wyatt, J. Org. Chem. 1996, 61, 7234;
24. d) M. E. Garcia, J. A. Gavin, N. Deng, A. A. Andrievsky, T. E. Mallouk, Tetrahedron Lett. 1996, 37, 8313;
25. e) M. Asakawa, P. R. Ashton, S. E. Boyd, C. L. Brown, S. Menzer, D. Pasini, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, P. G. Wyatt, Chem. Eur. J. 1997, 3, 463;
26. f) J. A. Gavin, M. E. Garcia, A. J. Benesi, T. E. Mallouk, J. Org. Chem. 1998, 63, 7663.
27. a) J. A. Clarke, O. Meth-Cohn, Tetrahedron Lett. 1975, 4705;
28. b) M. Hojjatie, S. Muralidharan, H. Freiser, Tetrahedron 1989, 45, 1611;
29. c) T. Dierick, D. De Schrijver, W. Eevers, H. J. Geise, Bull. Soc. Chim. Belg. 1991, 100, 631;
30. d) W. Eevers, D. De Schrijver, T. Dierick, C. Peten, J. Van der Looy, H. J. Geise, Synth. Met. 1992, 51, 329;
31. e) P. S. Chen, C. H. Chou, J. Chin. Chem. Soc. (Taipei) 1992, 39, 251.
32. E. D. Bergmann, Z. Pelchowicz, J. Am. Chem. Soc. 1953, 75, 4281.
33. a) W. Baker, K. M. Buggle, J. F. W. McOmie, D. A. M. Watkins, J. Chem. Soc. 1958, 3594;
34. b) M. Newcomb, G. W. Gokel, D. J. Cram, J. Am. Chem. Soc. 1974, 96, 6810.
35. C. Bilger, R. Royer, P. Demerseman, Synthesis 1988, 902.
36. P. R. Ashton, J. A. Preece, J. F. Stoddart, M. S. Tolley, A. J. P. White, D. J. Williams, Synthesis 1994, 1344.
37. W. Geuder, S. Hünig, A. Suchy, Tetrahedron 1986, 42, 1665.
38. H. Scheytza, O. Rademacher, H.-U. Reissig, Chem. Eur. J., submitted.
39. a) A. Lubbineau, J. Augé, Y. Queneau, Synthesis 1994, 741;
40. b) C.-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media, John Wiley & Sons, Inc. New York 1997.
41. a) W. Ried, J. Grabosch, Chem. Ber. 1958, 91, 2489;
42. b) G. Dyker, R. P. Kreher, Chem. Ber. 1988, 121, 1203;
43. c) B. Iddon, A. D. Redhouse, P. N. Yat, J. Chem. Soc., Perkin Trans, 1 1990, 1083.
44. H. Scheytza, H.-U. Reissig, Tetrahedron 1999, 55, 1057.
45. 6]DMSO).
46. H. Scheytza, L. Dunsch, manuscript in preparation.
47. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications no. CCDC-103287. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44) 1223 336-033; e-mail: deposit@ccdc.cam.ac.uk.).
48. a) G. M. Sheldrick, SHELXS-97, Program for the Solution of Crystal Structures, Universität Göttingen, 1997;
49. b) G. M. Sheldrick, SHELXL-97, Universität Göttingen, 1997.