Catalysis by Organic Solids. Stereoselective Intramolecular Ene Reaction of Citronellal Promoted by Microporous Molecular Crystals Having an Extensive Hydrogen-Bonded Network

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 12, 1997, Pages 3075-3079

  Sawaki, Tomoya ^a   Endo, Ken ^a,c   Kobayashi, Kenji ^b   Hayashida, Osamu ^a,c   Aoyama, Yasuhiro ^a,c  

^a KYUSHU UNIVERSITY   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

^c JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000380352     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.3075     Document Type: Article

References (44)

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12. For recent literatures very briefly referring to apparently catalytic behaviors of organic crystals, see: a) F. Toda, K. Tanaka, and A. Sekikawa, J. Chem. Soc., Chem. Commun., 1987, 279; b) K. Soai and M. Watanabe, J. Chem. Soc., Chem. Commun., 1990, 43; c) M. Fujita, Y. J. Kwon, S. Washuzu, and K. Ogura, J. Am. Chem. Soc., 116, 1151 (1994).
13. For recent literatures very briefly referring to apparently catalytic behaviors of organic crystals, see: a) F. Toda, K. Tanaka, and A. Sekikawa, J. Chem. Soc., Chem. Commun., 1987, 279; b) K. Soai and M. Watanabe, J. Chem. Soc., Chem. Commun., 1990, 43; c) M. Fujita, Y. J. Kwon, S. Washuzu, and K. Ogura, J. Am. Chem. Soc., 116, 1151 (1994).
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17. Selected examples are: a) R. M. Barrer and V. H. Shanson, J. Chem. Soc., Chem. Commun., 1976, 333; b) O. Ermer, J. Am. Chem Soc., 110, 3747 (1988); c) E. Weber, R. Pollex, and M. Czugler, J. Org. Chem., 57, 4068 (1992); d) S. B. Copp, S. Subramanian, and M. J. Zaworotko, J. Org. Chem., 114, 8719 (1992); e) D. S. Reddy, D. C. Craig, A. D. Rae, and G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1993, 1737; f) X. Wang, M. Simard, and J. D. Wuest, J. Am. Chem. Soc., 116, 12119 (1994); g) D. Venkataraman, S. Lee, J. Zhang, and J. S. Moore, Nature, 371, 591 (1994); h) D. S. Reddy, D. C. Craig, and G. R. Desiraju, J. Am. Chem. Soc., 118 4090 (1996).
18. Selected examples are: a) R. M. Barrer and V. H. Shanson, J. Chem. Soc., Chem. Commun., 1976, 333; b) O. Ermer, J. Am. Chem Soc., 110, 3747 (1988); c) E. Weber, R. Pollex, and M. Czugler, J. Org. Chem., 57, 4068 (1992); d) S. B. Copp, S. Subramanian, and M. J. Zaworotko, J. Org. Chem., 114, 8719 (1992); e) D. S. Reddy, D. C. Craig, A. D. Rae, and G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1993, 1737; f) X. Wang, M. Simard, and J. D. Wuest, J. Am. Chem. Soc., 116, 12119 (1994); g) D. Venkataraman, S. Lee, J. Zhang, and J. S. Moore, Nature, 371, 591 (1994); h) D. S. Reddy, D. C. Craig, and G. R. Desiraju, J. Am. Chem. Soc., 118 4090 (1996).
19. Selected examples are: a) R. M. Barrer and V. H. Shanson, J. Chem. Soc., Chem. Commun., 1976, 333; b) O. Ermer, J. Am. Chem Soc., 110, 3747 (1988); c) E. Weber, R. Pollex, and M. Czugler, J. Org. Chem., 57, 4068 (1992); d) S. B. Copp, S. Subramanian, and M. J. Zaworotko, J. Org. Chem., 114, 8719 (1992); e) D. S. Reddy, D. C. Craig, A. D. Rae, and G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1993, 1737; f) X. Wang, M. Simard, and J. D. Wuest, J. Am. Chem. Soc., 116, 12119 (1994); g) D. Venkataraman, S. Lee, J. Zhang, and J. S. Moore, Nature, 371, 591 (1994); h) D. S. Reddy, D. C. Craig, and G. R. Desiraju, J. Am. Chem. Soc., 118 4090 (1996).
20. Selected examples are: a) R. M. Barrer and V. H. Shanson, J. Chem. Soc., Chem. Commun., 1976, 333; b) O. Ermer, J. Am. Chem Soc., 110, 3747 (1988); c) E. Weber, R. Pollex, and M. Czugler, J. Org. Chem., 57, 4068 (1992); d) S. B. Copp, S. Subramanian, and M. J. Zaworotko, J. Org. Chem., 114, 8719 (1992); e) D. S. Reddy, D. C. Craig, A. D. Rae, and G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1993, 1737; f) X. Wang, M. Simard, and J. D. Wuest, J. Am. Chem. Soc., 116, 12119 (1994); g) D. Venkataraman, S. Lee, J. Zhang, and J. S. Moore, Nature, 371, 591 (1994); h) D. S. Reddy, D. C. Craig, and G. R. Desiraju, J. Am. Chem. Soc., 118 4090 (1996).
21. Selected examples are: a) R. M. Barrer and V. H. Shanson, J. Chem. Soc., Chem. Commun., 1976, 333; b) O. Ermer, J. Am. Chem Soc., 110, 3747 (1988); c) E. Weber, R. Pollex, and M. Czugler, J. Org. Chem., 57, 4068 (1992); d) S. B. Copp, S. Subramanian, and M. J. Zaworotko, J. Org. Chem., 114, 8719 (1992); e) D. S. Reddy, D. C. Craig, A. D. Rae, and G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1993, 1737; f) X. Wang, M. Simard, and J. D. Wuest, J. Am. Chem. Soc., 116, 12119 (1994); g) D. Venkataraman, S. Lee, J. Zhang, and J. S. Moore, Nature, 371, 591 (1994); h) D. S. Reddy, D. C. Craig, and G. R. Desiraju, J. Am. Chem. Soc., 118 4090 (1996).
22. Selected examples are: a) R. M. Barrer and V. H. Shanson, J. Chem. Soc., Chem. Commun., 1976, 333; b) O. Ermer, J. Am. Chem Soc., 110, 3747 (1988); c) E. Weber, R. Pollex, and M. Czugler, J. Org. Chem., 57, 4068 (1992); d) S. B. Copp, S. Subramanian, and M. J. Zaworotko, J. Org. Chem., 114, 8719 (1992); e) D. S. Reddy, D. C. Craig, A. D. Rae, and G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1993, 1737; f) X. Wang, M. Simard, and J. D. Wuest, J. Am. Chem. Soc., 116, 12119 (1994); g) D. Venkataraman, S. Lee, J. Zhang, and J. S. Moore, Nature, 371, 591 (1994); h) D. S. Reddy, D. C. Craig, and G. R. Desiraju, J. Am. Chem. Soc., 118 4090 (1996).
23. Selected examples are: a) R. M. Barrer and V. H. Shanson, J. Chem. Soc., Chem. Commun., 1976, 333; b) O. Ermer, J. Am. Chem Soc., 110, 3747 (1988); c) E. Weber, R. Pollex, and M. Czugler, J. Org. Chem., 57, 4068 (1992); d) S. B. Copp, S. Subramanian, and M. J. Zaworotko, J. Org. Chem., 114, 8719 (1992); e) D. S. Reddy, D. C. Craig, A. D. Rae, and G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1993, 1737; f) X. Wang, M. Simard, and J. D. Wuest, J. Am. Chem. Soc., 116, 12119 (1994); g) D. Venkataraman, S. Lee, J. Zhang, and J. S. Moore, Nature, 371, 591 (1994); h) D. S. Reddy, D. C. Craig, and G. R. Desiraju, J. Am. Chem. Soc., 118 4090 (1996).
24. Selected examples are: a) R. M. Barrer and V. H. Shanson, J. Chem. Soc., Chem. Commun., 1976, 333; b) O. Ermer, J. Am. Chem Soc., 110, 3747 (1988); c) E. Weber, R. Pollex, and M. Czugler, J. Org. Chem., 57, 4068 (1992); d) S. B. Copp, S. Subramanian, and M. J. Zaworotko, J. Org. Chem., 114, 8719 (1992); e) D. S. Reddy, D. C. Craig, A. D. Rae, and G. R. Desiraju, J. Chem. Soc., Chem. Commun., 1993, 1737; f) X. Wang, M. Simard, and J. D. Wuest, J. Am. Chem. Soc., 116, 12119 (1994); g) D. Venkataraman, S. Lee, J. Zhang, and J. S. Moore, Nature, 371, 591 (1994); h) D. S. Reddy, D. C. Craig, and G. R. Desiraju, J. Am. Chem. Soc., 118 4090 (1996).
25. For a list of recent literatures on the formation of ordered crystal structures involving hydrogen-bonded 1D, 2D, and 3D motifs, see: Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, and H. Masuda, J. Am. Chem. Soc., 118, 5562 (1996). Also see: a) J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383 (1994); b) S. Valiyaveettil, V. Enkelmann, and K. MŸlln, J. Chem. Soc., Chem. Commun., 1994, 2097; c) M. W. Hosseini, R. Ruppert, P. Schaeffer, A. De Cian, N. Kyritsakas, and J. Fischer, J. Chem. Soc., Chem. Commun., 1994, 2135. For examples of (infinite) metal-coodination networks, see: d) B. F. Abrahams, B. F. Hoskins, J. Liu, and R. Robson, J. Am. Chem. Soc., 113, 3045 (1991); e) Ref. 3c; f) Ref. 5d; g) P. J. Stang, D. H. Cao, S. Saito, and A. M. Arif, J. Am. Chem. Soc., 117, 6273 (1995); h) M. Fujita, Y. J. Kwon, O. Sasaki, K. Yamaguchi, and K. Ogura, J. Am. Chem. Soc., 117, 7287 (1995).
26. For a list of recent literatures on the formation of ordered crystal structures involving hydrogen-bonded 1D, 2D, and 3D motifs, see: Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, and H. Masuda, J. Am. Chem. Soc., 118, 5562 (1996). Also see: a) J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383 (1994); b) S. Valiyaveettil, V. Enkelmann, and K. MŸlln, J. Chem. Soc., Chem. Commun., 1994, 2097; c) M. W. Hosseini, R. Ruppert, P. Schaeffer, A. De Cian, N. Kyritsakas, and J. Fischer, J. Chem. Soc., Chem. Commun., 1994, 2135. For examples of (infinite) metal-coodination networks, see: d) B. F. Abrahams, B. F. Hoskins, J. Liu, and R. Robson, J. Am. Chem. Soc., 113, 3045 (1991); e) Ref. 3c; f) Ref. 5d; g) P. J. Stang, D. H. Cao, S. Saito, and A. M. Arif, J. Am. Chem. Soc., 117, 6273 (1995); h) M. Fujita, Y. J. Kwon, O. Sasaki, K. Yamaguchi, and K. Ogura, J. Am. Chem. Soc., 117, 7287 (1995).
27. For a list of recent literatures on the formation of ordered crystal structures involving hydrogen-bonded 1D, 2D, and 3D motifs, see: Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, and H. Masuda, J. Am. Chem. Soc., 118, 5562 (1996). Also see: a) J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383 (1994); b) S. Valiyaveettil, V. Enkelmann, and K. MŸlln, J. Chem. Soc., Chem. Commun., 1994, 2097; c) M. W. Hosseini, R. Ruppert, P. Schaeffer, A. De Cian, N. Kyritsakas, and J. Fischer, J. Chem. Soc., Chem. Commun., 1994, 2135. For examples of (infinite) metal-coodination networks, see: d) B. F. Abrahams, B. F. Hoskins, J. Liu, and R. Robson, J. Am. Chem. Soc., 113, 3045 (1991); e) Ref. 3c; f) Ref. 5d; g) P. J. Stang, D. H. Cao, S. Saito, and A. M. Arif, J. Am. Chem. Soc., 117, 6273 (1995); h) M. Fujita, Y. J. Kwon, O. Sasaki, K. Yamaguchi, and K. Ogura, J. Am. Chem. Soc., 117, 7287 (1995).
28. For a list of recent literatures on the formation of ordered crystal structures involving hydrogen-bonded 1D, 2D, and 3D motifs, see: Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, and H. Masuda, J. Am. Chem. Soc., 118, 5562 (1996). Also see: a) J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383 (1994); b) S. Valiyaveettil, V. Enkelmann, and K. MŸlln, J. Chem. Soc., Chem. Commun., 1994, 2097; c) M. W. Hosseini, R. Ruppert, P. Schaeffer, A. De Cian, N. Kyritsakas, and J. Fischer, J. Chem. Soc., Chem. Commun., 1994, 2135. For examples of (infinite) metal-coodination networks, see: d) B. F. Abrahams, B. F. Hoskins, J. Liu, and R. Robson, J. Am. Chem. Soc., 113, 3045 (1991); e) Ref. 3c; f) Ref. 5d; g) P. J. Stang, D. H. Cao, S. Saito, and A. M. Arif, J. Am. Chem. Soc., 117, 6273 (1995); h) M. Fujita, Y. J. Kwon, O. Sasaki, K. Yamaguchi, and K. Ogura, J. Am. Chem. Soc., 117, 7287 (1995).
29. For a list of recent literatures on the formation of ordered crystal structures involving hydrogen-bonded 1D, 2D, and 3D motifs, see: Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, and H. Masuda, J. Am. Chem. Soc., 118, 5562 (1996). Also see: a) J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383 (1994); b) S. Valiyaveettil, V. Enkelmann, and K. MŸlln, J. Chem. Soc., Chem. Commun., 1994, 2097; c) M. W. Hosseini, R. Ruppert, P. Schaeffer, A. De Cian, N. Kyritsakas, and J. Fischer, J. Chem. Soc., Chem. Commun., 1994, 2135. For examples of (infinite) metal-coodination networks, see: d) B. F. Abrahams, B. F. Hoskins, J. Liu, and R. Robson, J. Am. Chem. Soc., 113, 3045 (1991); e) Ref. 3c; f) Ref. 5d; g) P. J. Stang, D. H. Cao, S. Saito, and A. M. Arif, J. Am. Chem. Soc., 117, 6273 (1995); h) M. Fujita, Y. J. Kwon, O. Sasaki, K. Yamaguchi, and K. Ogura, J. Am. Chem. Soc., 117, 7287 (1995).
30. For a list of recent literatures on the formation of ordered crystal structures involving hydrogen-bonded 1D, 2D, and 3D motifs, see: Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, and H. Masuda, J. Am. Chem. Soc., 118, 5562 (1996). Also see: a) J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383 (1994); b) S. Valiyaveettil, V. Enkelmann, and K. MŸlln, J. Chem. Soc., Chem. Commun., 1994, 2097; c) M. W. Hosseini, R. Ruppert, P. Schaeffer, A. De Cian, N. Kyritsakas, and J. Fischer, J. Chem. Soc., Chem. Commun., 1994, 2135. For examples of (infinite) metal-coodination networks, see: d) B. F. Abrahams, B. F. Hoskins, J. Liu, and R. Robson, J. Am. Chem. Soc., 113, 3045 (1991); e) Ref. 3c; f) Ref. 5d; g) P. J. Stang, D. H. Cao, S. Saito, and A. M. Arif, J. Am. Chem. Soc., 117, 6273 (1995); h) M. Fujita, Y. J. Kwon, O. Sasaki, K. Yamaguchi, and K. Ogura, J. Am. Chem. Soc., 117, 7287 (1995).
31. For a list of recent literatures on the formation of ordered crystal structures involving hydrogen-bonded 1D, 2D, and 3D motifs, see: Y. Aoyama, K. Endo, T. Anzai, Y. Yamaguchi, T. Sawaki, K. Kobayashi, N. Kanehisa, H. Hashimoto, Y. Kai, and H. Masuda, J. Am. Chem. Soc., 118, 5562 (1996). Also see: a) J. C. MacDonald and G. M. Whitesides, Chem. Rev., 94, 2383 (1994); b) S. Valiyaveettil, V. Enkelmann, and K. MŸlln, J. Chem. Soc., Chem. Commun., 1994, 2097; c) M. W. Hosseini, R. Ruppert, P. Schaeffer, A. De Cian, N. Kyritsakas, and J. Fischer, J. Chem. Soc., Chem. Commun., 1994, 2135. For examples of (infinite) metal-coodination networks, see: d) B. F. Abrahams, B. F. Hoskins, J. Liu, and R. Robson, J. Am. Chem. Soc., 113, 3045 (1991); e) Ref. 3c; f) Ref. 5d; g) P. J. Stang, D. H. Cao, S. Saito, and A. M. Arif, J. Am. Chem. Soc., 117, 6273 (1995); h) M. Fujita, Y. J. Kwon, O. Sasaki, K. Yamaguchi, and K. Ogura, J. Am. Chem. Soc., 117, 7287 (1995).
32. Cf. K. Endo, T. Ezuhara, M. Koyanagi, H. Masuda, and Y. Aoyama, J. Am. Chem. Soc., 119, 499 (1997).
33. a) Ref. 1; b) K. Kobayashi, K. Endo, Y. Aoyama, and H. Masuda, Tetrahedron Lett., 34, 7929 (1993).
34. K. Endo, T. Sawaki, M. Koyanagi, K. Kobayashi, H. Masuda, and Y. Aoyama, J. Am. Chem. Soc., 117, 8341 (1995).
35. K. Endo, T. Koike, T. Sawaki, O. Hayashida, H. Masuda, and Y. Aoyama, J. Am. Chem. Soc., 119, 4117 (1997).
36. w=0.099, GOF=1.48.
37. The anthracene and resorcinol rings in compound 1 are roughly orthogonal with a dihedral angle of 85°. The two resorcinol rings directly linked via a hydrogen bond are nearly coplanar with a tilt angle of 5°.
38. a) H. M. R. Hoffmann, Angew. Chem., Int. Ed. Engl., 8, 556 (1969);
39. b) W. Opplzer and V. Snieckus, Angew. Chem., Int. Ed. Engl., 17, 476 (1978).
40. Y. Nakatani and K. Kawashima, Synthesis, 1978, 147.
41. Guest binding to host 1 in the solid state shows remarkably sigmoidal binding isotherms (unpublished results).
42. Competitive cocrystallization of host 1 from an equimolar mixture of cyctronellal (2) and isopulegol (3) results in an almost exclusive formation of adduct 1·2(3).
43. We thought that the formation of fully-packed adduct 1·2(2) could be suppressed when a dilute solution of guest 2 in cyclohexane as an inert solvent was used. Under these conditions, the guest/host ratio could in fact be kept low (2/1 < 1). Actually, however, a lot of cyclohexane molecules were also coincluded to fill the cavities.
44. Full crystal data are deposited as Document No. 70044 at the Office of the Editor of Bull. Chem. Soc. Jpn.