Ship-in-a-bottle synthesis of otherwise labile cyclic trimers of siloxanes in a self-assembled coordination cage [13]

Journal of the American Chemical Society

Volumn 122, Issue 26, 2000, Pages 6311-6312

  Yoshizawa, Michito ^c   Kusukawa, Takahiro ^c   Fujita, Makoto ^a   Yamaguchi, Kentaro ^b  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

^b CHIBA UNIVERSITY   (Japan)

^c NONE

Author keywords

[No Author keywords available]

Indexed keywords

OLIGOMER; SILOXANE;

CHEMICAL REACTION; CHEMICAL STRUCTURE; ENCAPSULATION; LETTER; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034608851     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000779c     Document Type: Letter

References (35)

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18. Self-assembled cage compounds containing metals: (a) Mann, S.; Huttner, G.; Zsolnai, L.; Heinze, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 2808. (b) Jacopozzi, P.; Dalcanale, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 613. Hartshorn, C. M.; Steel, P. J. Chem. Commun. 1997, 541. Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975. (e) Linder, E.; Hermann, C; Baum, C.; Fenske, D. Eur. J. Inorg. Chem. 1999, 679. (f) Cotton, F. A.; Daniels, L. M.; Lin, C; Murillo, C. A. Chem. Commun. 1999, 841. (g) Fujita, M. Chem. Soc. Rev. 1998, 27, 417 and references therein.
19. Self-assembled cage compounds containing metals: (a) Mann, S.; Huttner, G.; Zsolnai, L.; Heinze, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 2808. (b) Jacopozzi, P.; Dalcanale, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 613. Hartshorn, C. M.; Steel, P. J. Chem. Commun. 1997, 541. Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975. (e) Linder, E.; Hermann, C; Baum, C.; Fenske, D. Eur. J. Inorg. Chem. 1999, 679. (f) Cotton, F. A.; Daniels, L. M.; Lin, C; Murillo, C. A. Chem. Commun. 1999, 841. (g) Fujita, M. Chem. Soc. Rev. 1998, 27, 417 and references therein.
20. Self-assembled cage compounds containing metals: (a) Mann, S.; Huttner, G.; Zsolnai, L.; Heinze, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 2808. (b) Jacopozzi, P.; Dalcanale, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 613. Hartshorn, C. M.; Steel, P. J. Chem. Commun. 1997, 541. Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975. (e) Linder, E.; Hermann, C; Baum, C.; Fenske, D. Eur. J. Inorg. Chem. 1999, 679. (f) Cotton, F. A.; Daniels, L. M.; Lin, C; Murillo, C. A. Chem. Commun. 1999, 841. (g) Fujita, M. Chem. Soc. Rev. 1998, 27, 417 and references therein.
21. Self-assembled cage compounds containing metals: (a) Mann, S.; Huttner, G.; Zsolnai, L.; Heinze, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 2808. (b) Jacopozzi, P.; Dalcanale, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 613. Hartshorn, C. M.; Steel, P. J. Chem. Commun. 1997, 541. Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975. (e) Linder, E.; Hermann, C; Baum, C.; Fenske, D. Eur. J. Inorg. Chem. 1999, 679. (f) Cotton, F. A.; Daniels, L. M.; Lin, C; Murillo, C. A. Chem. Commun. 1999, 841. (g) Fujita, M. Chem. Soc. Rev. 1998, 27, 417 and references therein.
22. Self-assembled cage compounds containing metals: (a) Mann, S.; Huttner, G.; Zsolnai, L.; Heinze, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 2808. (b) Jacopozzi, P.; Dalcanale, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 613. Hartshorn, C. M.; Steel, P. J. Chem. Commun. 1997, 541. Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975. (e) Linder, E.; Hermann, C; Baum, C.; Fenske, D. Eur. J. Inorg. Chem. 1999, 679. (f) Cotton, F. A.; Daniels, L. M.; Lin, C; Murillo, C. A. Chem. Commun. 1999, 841. (g) Fujita, M. Chem. Soc. Rev. 1998, 27, 417 and references therein.
23. Self-assembled cage compounds containing metals: (a) Mann, S.; Huttner, G.; Zsolnai, L.; Heinze, K. Angew. Chem., Int. Ed. Engl. 1996, 35, 2808. (b) Jacopozzi, P.; Dalcanale, E. Angew. Chem., Int. Ed. Engl. 1997, 36, 613. Hartshorn, C. M.; Steel, P. J. Chem. Commun. 1997, 541. Caulder, D. L.; Raymond, K. N. Acc. Chem. Res. 1999, 32, 975. (e) Linder, E.; Hermann, C; Baum, C.; Fenske, D. Eur. J. Inorg. Chem. 1999, 679. (f) Cotton, F. A.; Daniels, L. M.; Lin, C; Murillo, C. A. Chem. Commun. 1999, 841. (g) Fujita, M. Chem. Soc. Rev. 1998, 27, 417 and references therein.
24. Chemical transformation in self-assembled cage compounds: (a) Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50. (b) Kang, J.; Hilmersson, G.; Santameria, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650. Kang, J.; Santameria, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278. (e) Ito, H.; Kusukawa, T.; Fujita, M. Chem. Lett. In press.
25. Chemical transformation in self-assembled cage compounds: (a) Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50. (b) Kang, J.; Hilmersson, G.; Santameria, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650. Kang, J.; Santameria, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278. (e) Ito, H.; Kusukawa, T.; Fujita, M. Chem. Lett. In press.
26. Chemical transformation in self-assembled cage compounds: (a) Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50. (b) Kang, J.; Hilmersson, G.; Santameria, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650. Kang, J.; Santameria, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278. (e) Ito, H.; Kusukawa, T.; Fujita, M. Chem. Lett. In press.
27. Chemical transformation in self-assembled cage compounds: (a) Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50. (b) Kang, J.; Hilmersson, G.; Santameria, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650. Kang, J.; Santameria, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278. (e) Ito, H.; Kusukawa, T.; Fujita, M. Chem. Lett. In press.
28. Chemical transformation in self-assembled cage compounds: (a) Kang, J.; Rebek, J., Jr. Nature 1997, 385, 50. (b) Kang, J.; Hilmersson, G.; Santameria, J.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 3650. Kang, J.; Santameria, J.; Hilmersson, G.; Rebek, J., Jr. J. Am. Chem. Soc. 1998, 120, 7389. Rebek, J., Jr. Acc. Chem. Res. 1999, 32, 278. (e) Ito, H.; Kusukawa, T.; Fujita, M. Chem. Lett. In press.
29. "Ship-in-a-bottle" synthesis in the cuvity of zeolites has been reported: (a) Sheu, L. L.; Knozinger, H.; Sachtler, W. M. H. Catal. Lett. 1989, 2, 129. (b) Ichikawa, M. Adv. Catal. 1992, 38, 283 and references therein.
30. "Ship-in-a-bottle" synthesis in the cuvity of zeolites has been reported: (a) Sheu, L. L.; Knozinger, H.; Sachtler, W. M. H. Catal. Lett. 1989, 2, 129. (b) Ichikawa, M. Adv. Catal. 1992, 38, 283 and references therein.
31. 2 and tris(4-pyridyl)-1,3,5-triazine. This compound was shown to be stable under acidic and basic conditions. See Supporting Information.
32. Physical properties of 3·1a: See Supporting Information.
33. 2O) to give 3·1b as a pale yellow powder in 90% yield. Physical properties of 3·1b: See Supporting Information.
34. 3-symmetric structure.
35. The protection of 1b might be afforded by the pyridine ligands which may trap any protons trying to pass through the portal.