Multiply stranded and multiply encircled pseudorotaxanes

Journal of the American Chemical Society

Volumn 119, Issue 51, 1997, Pages 12514-12524

  Ashton, Peter R ^a   Fyfe, Matthew C T ^a   Glink, Peter T ^a   Menzer, Stephan ^b   Stoddart, J Fraser ^a,c   White, Andrew J P ^b   Williams, David J ^b  

^a UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

^c UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

TAXANE DERIVATIVE;

ARTICLE; HYDROGEN BOND; MOLECULAR INTERACTION; SYNTHESIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

EID: 0031585687     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9714806     Document Type: Article

References (31)

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5. Some recent examples serve to highlight the kinds of approaches being taken. See: (a) Fujita, M.; Ogura, D.; Miyazawa, M.; Oka, H.; Yamaguchi, K.; Ogura, K. Nature (London) 1995, 378, 469-471. (b) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (c) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095-1098. (d) Funeriu, D. P.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1997, 3, 99-104. (e) Meissner, R.; Gardas, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77-85. (f) Whang, D.; Kim, K. J. Am. Chem. Soc. 1997, 119, 451-452.
6. Some recent examples serve to highlight the kinds of approaches being taken. See: (a) Fujita, M.; Ogura, D.; Miyazawa, M.; Oka, H.; Yamaguchi, K.; Ogura, K. Nature (London) 1995, 378, 469-471. (b) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (c) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095-1098. (d) Funeriu, D. P.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1997, 3, 99-104. (e) Meissner, R.; Gardas, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77-85. (f) Whang, D.; Kim, K. J. Am. Chem. Soc. 1997, 119, 451-452.
7. Some recent examples serve to highlight the kinds of approaches being taken. See: (a) Fujita, M.; Ogura, D.; Miyazawa, M.; Oka, H.; Yamaguchi, K.; Ogura, K. Nature (London) 1995, 378, 469-471. (b) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (c) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095-1098. (d) Funeriu, D. P.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1997, 3, 99-104. (e) Meissner, R.; Gardas, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77-85. (f) Whang, D.; Kim, K. J. Am. Chem. Soc. 1997, 119, 451-452.
8. Some recent examples serve to highlight the kinds of approaches being taken. See: (a) Fujita, M.; Ogura, D.; Miyazawa, M.; Oka, H.; Yamaguchi, K.; Ogura, K. Nature (London) 1995, 378, 469-471. (b) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (c) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095-1098. (d) Funeriu, D. P.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1997, 3, 99-104. (e) Meissner, R.; Gardas, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77-85. (f) Whang, D.; Kim, K. J. Am. Chem. Soc. 1997, 119, 451-452.
9. Some recent examples serve to highlight the kinds of approaches being taken. See: (a) Fujita, M.; Ogura, D.; Miyazawa, M.; Oka, H.; Yamaguchi, K.; Ogura, K. Nature (London) 1995, 378, 469-471. (b) Hartgerink, J. D.; Granja, J. R.; Milligan, R. A.; Ghadiri, M. R. J. Am. Chem. Soc. 1996, 118, 43-50. (c) Zimmerman, S. C.; Zeng, F.; Reichert, D. E. C.; Kolotuchin, S. V. Science 1996, 271, 1095-1098. (d) Funeriu, D. P.; Lehn, J.-M.; Baum, G.; Fenske, D. Chem. Eur. J. 1997, 3, 99-104. (e) Meissner, R.; Gardas, X.; Mecozzi, S.; Rebek, J., Jr. J. Am. Chem. Soc. 1997, 119, 77-85. (f) Whang, D.; Kim, K. J. Am. Chem. Soc. 1997, 119, 451-452.
10. Amabilino, D. B.; Anelli, P.-L.; Ashton, P. R.; Brown, G. R.; Córdova, E.; Godínez, L. A.; Hayes, W.; Kaifer, A. E.; Philp, D.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Tolley, M. S.; Williams, D. J. J. Am. Chem. Soc. 1995, 117, 11142-11170.
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16. For instance, see: Ashton, P. R.; Ballardini, R.; Balzani, V.; Belohradsky, M.; Gandolfi, M. T.; Philp, D.; Prodi, L.; Raymo, F. M.; Reddington, M. V.; Spencer, N.; Stoddart, J. F.; Venturi, M.; Williams, D. J. J. Am. Chem. Soc. 1996, 118, 4931-4951.
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24. 2 in the absence of a suitably sized crown ether for complexation.
25. See the Supporting Information for details.
26. 2.
27. 2 at 20 °C these were 0.00, -0.17, -0.29, -0.36, and +0.13 ppm, respectively.
28. Fyfe, M. C. T.; Glink, P. T.; Menzer, S.; Stoddart, J. F.; White, A. J. P.; Williams, D. J. Angew. Chem., Int. Ed. Engl. 1997, 36, 2068-2070.
29. 24 "co-conformation" to designate the three-dimensional spatial arrangement of the atoms in suprameleeular systems.
30. 2 at 20 °C these were -0.03, -0.15, -0.23, -0.38, and +0.16 ppm, respectively.
31. SHELXTL PC version 5.03. Siemens Analytical X-Ray Instruments, Inc., Madison, WI, 1994.