A new cryptand: Synthesis and complexation with paraquat

Organic Letters

Volumn 1, Issue 7, 1999, Pages 1001-1004

  Bryant, William S ^a   Jones, Jason W ^a   Mason, Philip E ^a   Guzei, Ilia ^b   Rheingold, Arnold L ^b   Fronczek, Frank R ^c   Nagvekar, Devdatt S ^a   Gibson, Harry W ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^b UNIVERSITY OF DELAWARE   (United States)

^c LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ETHER DERIVATIVE; PARAQUAT;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; X RAY DIFFRACTION;

ETHERS, CYCLIC; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PARAQUAT; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; X-RAY DIFFRACTION;

EID: 0033533646     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990780k     Document Type: Article

References (39)

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9. Dietrich, B. In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Series Eds.; Pergamon Press: New York, 1996; Vol. 1, Gokel, G., Vol. Ed., Chapter 4, pp 153-211.
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12. The concept of preorganization can logically be traced to the "lock and key" idea of Fischer (Chem. Ber. 1894, 27, 2985). The enhanced effectiveness of macrocyclic hosts (coronands) over linear analogues (podands) (ref 1), the macrocyclic effect, suggested further improvements with cryptands. Further development included significant contributions from Cram ( Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, UK, 1994) and Lehn (ref 6). For a very instructive review of these concepts, see: Inoue, Y.; Wada, T. Adv. Supramol. Chem. 1997, 4, 55.
13. The concept of preorganization can logically be traced to the "lock and key" idea of Fischer (Chem. Ber. 1894, 27, 2985). The enhanced effectiveness of macrocyclic hosts (coronands) over linear analogues (podands) (ref 1), the macrocyclic effect, suggested further improvements with cryptands. Further development included significant contributions from Cram ( Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, UK, 1994) and Lehn (ref 6). For a very instructive review of these concepts, see: Inoue, Y.; Wada, T. Adv. Supramol. Chem. 1997, 4, 55.
14. The concept of preorganization can logically be traced to the "lock and key" idea of Fischer (Chem. Ber. 1894, 27, 2985). The enhanced effectiveness of macrocyclic hosts (coronands) over linear analogues (podands) (ref 1), the macrocyclic effect, suggested further improvements with cryptands. Further development included significant contributions from Cram ( Cram, D. J.; Cram, J. M. Container Molecules and Their Guests; Royal Society of Chemistry: Cambridge, UK, 1994) and Lehn (ref 6). For a very instructive review of these concepts, see: Inoue, Y.; Wada, T. Adv. Supramol. Chem. 1997, 4, 55.
15. Stoddart, F. Chem. Br. 1991, 714.
16. (a) Allwood, B. L.; Spencer, N.; Shahriari-Zavareh, H.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1987, 1058.
17. (b) Asakawa, M.; Ashton, P. R.; Ballardini, R.; Balzani, V.; Belohradsky, M.; Gandolfi, M. T.; Kocian, O.; Prodi, L.; Raymo, F. M.; Stoddart, J. F.; Venturi, M. J. Am. Chem. Soc. 1997, 119, 302.
18. Asakawa, M.; Ashton, P. R.; Boyd, S. E.; Brown, C. L.; Gillard, R. E.; Kocian, O.; Raymo, F. M.; Stoddart, J. F.; Tolley, M. S.; White, A. J. P.; Williams, D. J. J. Org. Chem. 1997, 62, 26 and references therein.
19. Reviews: Mahan, E.; Gibson, H. W., In Cyclic Polymers, 2nd ed.; Semlyen, A. J., Ed.; Thomson Science and Professional: London, UK, in press. Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 9, ASAP web posting June 11, 1999. Harada, A. Acta Polym. 1998, 49, 3. Gibson, H. W. In Large Ring Molecules; Semlyen, J. A., Ed.; John Wiley & Sons: New York, 1996; Chapter 6, pp 191-262. Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 1155.
20. Reviews: Mahan, E.; Gibson, H. W., In Cyclic Polymers, 2nd ed.; Semlyen, A. J., Ed.; Thomson Science and Professional: London, UK, in press. Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 9, ASAP web posting June 11, 1999. Harada, A. Acta Polym. 1998, 49, 3. Gibson, H. W. In Large Ring Molecules; Semlyen, J. A., Ed.; John Wiley & Sons: New York, 1996; Chapter 6, pp 191-262. Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 1155.
21. Reviews: Mahan, E.; Gibson, H. W., In Cyclic Polymers, 2nd ed.; Semlyen, A. J., Ed.; Thomson Science and Professional: London, UK, in press. Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 9, ASAP web posting June 11, 1999. Harada, A. Acta Polym. 1998, 49, 3. Gibson, H. W. In Large Ring Molecules; Semlyen, J. A., Ed.; John Wiley & Sons: New York, 1996; Chapter 6, pp 191-262. Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 1155.
22. Reviews: Mahan, E.; Gibson, H. W., In Cyclic Polymers, 2nd ed.; Semlyen, A. J., Ed.; Thomson Science and Professional: London, UK, in press. Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 9, ASAP web posting June 11, 1999. Harada, A. Acta Polym. 1998, 49, 3. Gibson, H. W. In Large Ring Molecules; Semlyen, J. A., Ed.; John Wiley & Sons: New York, 1996; Chapter 6, pp 191-262. Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 1155.
23. Reviews: Mahan, E.; Gibson, H. W., In Cyclic Polymers, 2nd ed.; Semlyen, A. J., Ed.; Thomson Science and Professional: London, UK, in press. Raymo, F. M.; Stoddart, J. F. Chem. Rev. 1999, 99, 9, ASAP web posting June 11, 1999. Harada, A. Acta Polym. 1998, 49, 3. Gibson, H. W. In Large Ring Molecules; Semlyen, J. A., Ed.; John Wiley & Sons: New York, 1996; Chapter 6, pp 191-262. Philp, D.; Stoddart, J. F. Angew. Chem., Int. Ed. Engl. 1996, 1155.
24. Bryant, W. S.; Guzei, I. A.; Rheingold, A. L.; Gibson, H. W. Org. Lett. 1999, 1, 47.
25. Delaviz, Y.; Gibson, H. W. Polym. Commun. 1991, 32, 103.
26. Gibson, H. W.; Nagvekar, D. S. Can. J. Chem. 1997, 75, 1375.
27. -3 for 5130 data having I > 2σ(I).
28. -3 for 5130 data having I > 2σ(I).
29. Fyfe, M. C. T.; Stoddart, J. F. Adv. Supramol. Chem. 1999, 5, 1.
30. Bisphenol 2d was derived from 5-benzyloxyresorcinol [Nagvekar, D.; Gibson, H. W. Org. Prep. Proced. Int. 1997, 29, 240] via 2c using the methodology reported for other derivatives of bis(m-phenylene)-32-crown-10 (ref 13). Details are given in the Supporting Information.
31. 15Na, 749.3373].
32. a of the uncomplexed cryptand 3 or crown ether 2b and the observed signals in the presence of varied amounts of 1a (titration).
33. Using the iterative Creswell-Allred method: Gong, C.; Balanda, P. B.; Gibson, H. W. Macromolecules 1998, 31, 5278.
34. Tsukube, H.; Furuta, H.; Odani, A.; Takeda, Y.; Kudo, Y.; Inoue, Y.; Liu, Y.; Sakamoto, H.; Kimura, K., In Comprehensive Supramolecular Chemistry; Atwood, J. L., Davies, J. E. D., MacNicol, D. D., Vögtle, F., Series Eds.; Pergamon Press: New York, 1996; Vol. 8, Davies, J. E. D., Ripmeester, J. A., Vol. Eds., Chapter 10, pp 425-482.
35. 3, room temperture). It should be noted that this host is also a cryptand containing a very strong electron donor, the porphyrin unit.
36. 3, room temperture). It should be noted that this host is also a cryptand containing a very strong electron donor, the porphyrin unit.
37. This term was used by Stoddart et al. to describe analogous inclusion complexes of 1a and 1b with bis(p-phenylene)-34-crown-10 (BMP34C10) (Ashton, P. R.; Philp, D.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1991, 1680 ). A referee suggested that 1a:3 is not a "true" pseudorotaxane because 1a is not long enough to extend outside the cavity of 3. This is a somewhat subjective point since the methyl groups of 1a protrude only slightly from the cavity. In the case of 1b:3, however, 1b is long enough to do so, as clearly shown by single-crystal X-ray analyses with BMP34C10 in our own work (Shen, Y. X.; Engen, P. T.; Gibson, H. W.; Merola, J. S. Abstracts of Papers, 201st National Meeting of the American Chemical Society, Atlanta, GA, April 1991; American Chemical Society: Washington, DC, 1991: ORGN 325. Shen, Y. X.; Engen, P. T.; Berg, M. A. G.; Merola, J. S.; Gibson, H. W. Macromolecules 1992, 25, 2786) and that of Stoddart (above reference). We thus anticipate that 1b:3 is a "true" pseudorotaxane.
38. This term was used by Stoddart et al. to describe analogous inclusion complexes of 1a and 1b with bis(p-phenylene)-34-crown-10 (BMP34C10) (Ashton, P. R.; Philp, D.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1991, 1680 ). A referee suggested that 1a:3 is not a "true" pseudorotaxane because 1a is not long enough to extend outside the cavity of 3. This is a somewhat subjective point since the methyl groups of 1a protrude only slightly from the cavity. In the case of 1b:3, however, 1b is long enough to do so, as clearly shown by single-crystal X-ray analyses with BMP34C10 in our own work (Shen, Y. X.; Engen, P. T.; Gibson, H. W.; Merola, J. S. Abstracts of Papers, 201st National Meeting of the American Chemical Society, Atlanta, GA, April 1991; American Chemical Society: Washington, DC, 1991: ORGN 325. Shen, Y. X.; Engen, P. T.; Berg, M. A. G.; Merola, J. S.; Gibson, H. W. Macromolecules 1992, 25, 2786) and that of Stoddart (above reference). We thus anticipate that 1b:3 is a "true" pseudorotaxane.
39. This term was used by Stoddart et al. to describe analogous inclusion complexes of 1a and 1b with bis(p-phenylene)-34-crown-10 (BMP34C10) (Ashton, P. R.; Philp, D.; Reddington, M. V.; Slawin, A. M. Z.; Spencer, N.; Stoddart, J. F.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1991, 1680 ). A referee suggested that 1a:3 is not a "true" pseudorotaxane because 1a is not long enough to extend outside the cavity of 3. This is a somewhat subjective point since the methyl groups of 1a protrude only slightly from the cavity. In the case of 1b:3, however, 1b is long enough to do so, as clearly shown by single-crystal X-ray analyses with BMP34C10 in our own work (Shen, Y. X.; Engen, P. T.; Gibson, H. W.; Merola, J. S. Abstracts of Papers, 201st National Meeting of the American Chemical Society, Atlanta, GA, April 1991; American Chemical Society: Washington, DC, 1991: ORGN 325. Shen, Y. X.; Engen, P. T.; Berg, M. A. G.; Merola, J. S.; Gibson, H. W. Macromolecules 1992, 25, 2786) and that of Stoddart (above reference). We thus anticipate that 1b:3 is a "true" pseudorotaxane.