Catenanes and rotaxanes of the amide type

Pure and Applied Chemistry

Volumn 68, Issue 2, 1996, Pages 225-232

  Vogtle F ^a   Jager R ^a   Handel M ^a   Ottens Hildebrandt, S ^a  

^a UNIVERSITY OF BONN   (Germany)

Author keywords

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Indexed keywords

EID: 0040530095     PISSN: 00334545     EISSN: None     Source Type: Journal    
DOI: 10.1351/pac199668020225     Document Type: Article

References (36)

1. a) For earlier catenanes see G. Schill, N. Schweickert, H. Fritz and W. Vetter, Angew. Chem. 95, 909 (1983); Angew. Chem. Int. Ed. Engl. 22, 889 (1983); Chem. Ber. 121, 961 (1988); D.M. Walba, R.M. Richards, M. Hermsmeier and R.C. Haltiwanger, J. Am. Chem. Soc. 109, 7081 (1987); D.M. Walba, Q.Y. Zheng and K. Schilling, J. Am. Chem. Soc. 114, 6259 (1992).
2. a) For earlier catenanes see G. Schill, N. Schweickert, H. Fritz and W. Vetter, Angew. Chem. 95, 909 (1983); Angew. Chem. Int. Ed. Engl. 22, 889 (1983); Chem. Ber. 121, 961 (1988); D.M. Walba, R.M. Richards, M. Hermsmeier and R.C. Haltiwanger, J. Am. Chem. Soc. 109, 7081 (1987); D.M. Walba, Q.Y. Zheng and K. Schilling, J. Am. Chem. Soc. 114, 6259 (1992).
3. a) For earlier catenanes see G. Schill, N. Schweickert, H. Fritz and W. Vetter, Angew. Chem. 95, 909 (1983); Angew. Chem. Int. Ed. Engl. 22, 889 (1983); Chem. Ber. 121, 961 (1988); D.M. Walba, R.M. Richards, M. Hermsmeier and R.C. Haltiwanger, J. Am. Chem. Soc. 109, 7081 (1987); D.M. Walba, Q.Y. Zheng and K. Schilling, J. Am. Chem. Soc. 114, 6259 (1992).
4. a) For earlier catenanes see G. Schill, N. Schweickert, H. Fritz and W. Vetter, Angew. Chem. 95, 909 (1983); Angew. Chem. Int. Ed. Engl. 22, 889 (1983); Chem. Ber. 121, 961 (1988); D.M. Walba, R.M. Richards, M. Hermsmeier and R.C. Haltiwanger, J. Am. Chem. Soc. 109, 7081 (1987); D.M. Walba, Q.Y. Zheng and K. Schilling, J. Am. Chem. Soc. 114, 6259 (1992).
5. a) For earlier catenanes see G. Schill, N. Schweickert, H. Fritz and W. Vetter, Angew. Chem. 95, 909 (1983); Angew. Chem. Int. Ed. Engl. 22, 889 (1983); Chem. Ber. 121, 961 (1988); D.M. Walba, R.M. Richards, M. Hermsmeier and R.C. Haltiwanger, J. Am. Chem. Soc. 109, 7081 (1987); D.M. Walba, Q.Y. Zheng and K. Schilling, J. Am. Chem. Soc. 114, 6259 (1992).
6. b) See for example C.O. Dietrich-Buchecker, J. Guilhem, C. Pascard and J.-P. Sauvage, Angew. Chem. 102, 1202 (1990), Angew. Chem. Int. Ed. Engl. 29, 1154 (1990).
7. b) See for example C.O. Dietrich-Buchecker, J. Guilhem, C. Pascard and J.-P. Sauvage, Angew. Chem. 102, 1202 (1990), Angew. Chem. Int. Ed. Engl. 29, 1154 (1990).
8. c) P.R. Ashton, T.T. Goodnow, A.E. Kaifer, M.V. Reddington, A.M.Z. Slawin, N. Spencer, J.F. Stoddart, C. Vincent and D.J. Williams, Angew. Chem. 101, 1404 (1989); Angew. Chem. Int. Ed. Engl. 28, 1396 (1989); D. Philp and J.F. Stoddart, Synlett 1991, 445.
9. c) P.R. Ashton, T.T. Goodnow, A.E. Kaifer, M.V. Reddington, A.M.Z. Slawin, N. Spencer, J.F. Stoddart, C. Vincent and D.J. Williams, Angew. Chem. 101, 1404 (1989); Angew. Chem. Int. Ed. Engl. 28, 1396 (1989); D. Philp and J.F. Stoddart, Synlett 1991, 445.
10. c) P.R. Ashton, T.T. Goodnow, A.E. Kaifer, M.V. Reddington, A.M.Z. Slawin, N. Spencer, J.F. Stoddart, C. Vincent and D.J. Williams, Angew. Chem. 101, 1404 (1989); Angew. Chem. Int. Ed. Engl. 28, 1396 (1989); D. Philp and J.F. Stoddart, Synlett 1991, 445.
11. d) M. Fujita, F. Ibukura, K. Yamaguchi and K Ogura, J. Am. Chem. Soc. 117, 4175 (1995).
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13. G.-J.M. Gruter, F.J.J. de Kanter, P.R. Markies, T. Nomoto, O.S. Akkerman and F. Bickelhaupt, J. Am. Chem. Soc. 115, 12179 (1993).
14. f) Y. Geerts, D. Muscat and K. Müllen, Macrom. Chem. Phys. 1995, submitted.
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16. R. Hoss and F. Vögtle, Angew. Chem. 106, 389 (1994), Angew. Chem. Int. Ed. Engl. 33, 375 (1994); S. Anderson, H.L. Anderson and J.K.M. Sanders, Angew. Chem. 104, 921 (1992), Angew. Chem. Int. Ed. Engl. 31, 907 (1992); S. Anderson, H.L. Anderson and J.K.M. Sanders, Ace. Chem. Res. 26, 469 (1993).
17. R. Hoss and F. Vögtle, Angew. Chem. 106, 389 (1994), Angew. Chem. Int. Ed. Engl. 33, 375 (1994); S. Anderson, H.L. Anderson and J.K.M. Sanders, Angew. Chem. 104, 921 (1992), Angew. Chem. Int. Ed. Engl. 31, 907 (1992); S. Anderson, H.L. Anderson and J.K.M. Sanders, Ace. Chem. Res. 26, 469 (1993).
18. R. Hoss and F. Vögtle, Angew. Chem. 106, 389 (1994), Angew. Chem. Int. Ed. Engl. 33, 375 (1994); S. Anderson, H.L. Anderson and J.K.M. Sanders, Angew. Chem. 104, 921 (1992), Angew. Chem. Int. Ed. Engl. 31, 907 (1992); S. Anderson, H.L. Anderson and J.K.M. Sanders, Ace. Chem. Res. 26, 469 (1993).
19. R. Hoss and F. Vögtle, Angew. Chem. 106, 389 (1994), Angew. Chem. Int. Ed. Engl. 33, 375 (1994); S. Anderson, H.L. Anderson and J.K.M. Sanders, Angew. Chem. 104, 921 (1992), Angew. Chem. Int. Ed. Engl. 31, 907 (1992); S. Anderson, H.L. Anderson and J.K.M. Sanders, Ace. Chem. Res. 26, 469 (1993).
20. R. Hoss and F. Vögtle, Angew. Chem. 106, 389 (1994), Angew. Chem. Int. Ed. Engl. 33, 375 (1994); S. Anderson, H.L. Anderson and J.K.M. Sanders, Angew. Chem. 104, 921 (1992), Angew. Chem. Int. Ed. Engl. 31, 907 (1992); S. Anderson, H.L. Anderson and J.K.M. Sanders, Ace. Chem. Res. 26, 469 (1993).
21. L. Wambach and F. Vögtle, Tetrahedron Lett. 26, 1483 (1985); B. Dung and F. Vögtle, J. Incl. Phenom. 6, 429 (1988); J. Breitenbach, K. Rissanen, U.U. Wolf and F. Vögtle, Chem. Ber. 124, 2323 (1991);
22. L. Wambach and F. Vögtle, Tetrahedron Lett. 26, 1483 (1985); B. Dung and F. Vögtle, J. Incl. Phenom. 6, 429 (1988); J. Breitenbach, K. Rissanen, U.U. Wolf and F. Vögtle, Chem. Ber. 124, 2323 (1991);
23. L. Wambach and F. Vögtle, Tetrahedron Lett. 26, 1483 (1985); B. Dung and F. Vögtle, J. Incl. Phenom. 6, 429 (1988); J. Breitenbach, K. Rissanen, U.U. Wolf and F. Vögtle, Chem. Ber. 124, 2323 (1991);
24. C. Seel and F. Vögtle, in Perspectives in Coordination Chemistry (Eds.: A.F. Williams, C. Floriani, A.E. Merbach), p.31, VCH, Weinheim (1992).
25. F. Vögtle, S. Meier and R. Hoss, Angew. Chem. 104, 1628 (1992); Angew. Chem. Int. Ed. Engl. 31, 1619 (1992).
26. F. Vögtle, S. Meier and R. Hoss, Angew. Chem. 104, 1628 (1992); Angew. Chem. Int. Ed. Engl. 31, 1619 (1992).
27. Catenane 3 with R = H was independently prepared with remarkable yield (34%) in a two step synthesis starting from the isolated intermediate 13 and isophthaloyl dichloride 11: C.A. Hunter, J. Am. Chem. Soc. 114, 5303 (1992); see also C.A. Hunter and D.H. Purvis, Angew. Chem. 104, 779 (1992), Angew. Chem. Int. Ed. Engl. 31, 792 (1992).
28. Catenane 3 with R = H was independently prepared with remarkable yield (34%) in a two step synthesis starting from the isolated intermediate 13 and isophthaloyl dichloride 11: C.A. Hunter, J. Am. Chem. Soc. 114, 5303 (1992); see also C.A. Hunter and D.H. Purvis, Angew. Chem. 104, 779 (1992), Angew. Chem. Int. Ed. Engl. 31, 792 (1992).
29. Catenane 3 with R = H was independently prepared with remarkable yield (34%) in a two step synthesis starting from the isolated intermediate 13 and isophthaloyl dichloride 11: C.A. Hunter, J. Am. Chem. Soc. 114, 5303 (1992); see also C.A. Hunter and D.H. Purvis, Angew. Chem. 104, 779 (1992), Angew. Chem. Int. Ed. Engl. 31, 792 (1992).
30. S. Ottens-Hildebrandt, S. Meier, W. Schmidt and F. Vögtle, Angew. Chem. 106, 1818 (1994), Angew. Chem. Int. Ed. Engl. 33, 1767 (1994).
31. S. Ottens-Hildebrandt, S. Meier, W. Schmidt and F. Vögtle, Angew. Chem. 106, 1818 (1994), Angew. Chem. Int. Ed. Engl. 33, 1767 (1994).
32. S. Ottens-Hildebrandt. M. Nieger, K. Rissanen, J. Rouvinen, S. Meier, G. Harder and F. Vögtle, J. Chem. Soc., Chem. Commun. 1995, 777.
33. F. Vögtle, M. Händel, S. Meier, S. Ottens-Hildebrandt, F. Ott and T. Schmidt, Liebigs Ann. 1995, 739.
34. We express our gratitude to Dipl.-Chem. J. Osterodt, Universität Bonn, for the preparation of the computer-generated model; MM+: Autodesk HyperChem™ 2.0; N.L. Allinger, J. Am. Chem. Soc. 99, 8127 (1977).
35. In preliminary experiments we were already able to introduce building units such as sulfonamide groups (11), terephthalic acid units, podand units and deuterium labels.
36. S. Ottens-Hildebrandt, T. Schmidt, J. Harren and F. Vötle, Liebigs Ann. 1995, in press.