Topochemical transketalization reaction driven by hydrogen bonding

Journal of the American Chemical Society

Volumn 126, Issue 30, 2004, Pages 9174-9175

  Sureshan, Kana M ^a   Murakami, Tomohiro ^a   Miyasou, Tomomi ^a   Watanabe, Yutaka ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CATALYST; CHEMICAL REACTION; CRYSTAL STRUCTURE; DECOMPOSITION; HYDROGEN BOND; MELTING POINT; PHASE TRANSITION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SOLID STATE; TOPOCHEMICAL TRANSKETALIZATION;

EID: 3342908472     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0483847     Document Type: Article

References (36)

1. (a) Photochemistry in Organized and Constrained Media; Ramamurthy, V., Ed.; VCH Publishers: New York, 1991.
2. (b) Gamlin, J. N.; Jones, R.; Leibovitch, M.; Patrick, B.; Scheffer, J. R.; Trotter, J. Acc. Chem. Res. 1996, 29, 203.
3. (c) Hasegawa, M. Chem. Rev. 1983, 83, 507.
4. (d) Ramamurthy, V.; Venkatesan, K. Chem. Rev. 1987, 87, 433.
5. (e) Toda, F. Synlett 1992, 303.
6. (f) Singh, N. B.; Singh, R. J.; Singh, R. P. Tetrahedron 1994, 50, 6441.
7. (g) Green, B. S.; Lahav, M.; Rabinovich, D. Acc. Chem. Res. 1979, 12, 191.
8. For unimolecular topochemical reactions, see: (a) Choi, T.; Peterfy, K.; Khan, S. I.; Garcia-Garibay, M. A. J. Am. Chem. Soc. 1996, 118, 12477.
9. (b) Leibovitch, M.; Olovsson, G.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1998, 120, 12755.
10. (c) Garcia-Garibay, M. A.; Shin, S.; Sanrame, C. N. Tetrahedron 2000, 56, 6729.
11. (d) Sakamoto, M.; Takahashi, M.; Arai, W.; Mino, T.; Yamaguchi, K.; Watanabe, S.; Fujita, T. Tetrahedron 2000, 56, 6795.
12. (e) Takahashi, M.; Sekine, N.; Fujita, T.; Watanabe, S.; Yamaguchi, K.; Sakamoto, M. J. Am. Chem. Soc. 1998, 120, 12770.
13. (f) Cheung, E.; Rademacher, K.; Scheffer, J. R.; Trotter, J. Tetrahedron 2000, 56, 6739.
14. (g) Sekine, A.; Hori, K.; Ohashi, Y.; Yagi, M.; Toda, F. J. Am. Chem. Soc. 1989, 111, 697.
15. (a) Turowska-Tyrk, I. Chem. Eur. J. 2001, 3401.
16. (b) Tanaka, K.; Mochizuki, E.; Yasui, N.; Kai, Y.; Miyahara, I.; Hirotsu, K.; Toda, F. Tetrahedron 2000, 56, 6853.
17. (c) Honda, K.; Nakanishi, F.; Feeder, N. J. Am. Chem. Soc. 1999, 121, 8246.
18. (d) Tanaka, K.; Toda, F.; Mochizuki, E.; Kai, Y.; Miyahara, I.; Hirotsu, K. Angew. Chem., Int. Ed. 1999, 38, 3523.
19. (e) Kim, J. H.; Lindeman, S. V.; Kochi, J. K. J. Am. Chem. Soc. 2001, 123, 4951.
20. (a) Matsumoto, A.; Tanaka, T.; Tsubouchi, T.; Tashiro, K.; Saragai, S.; Nakamoto, S. J. Am. Chem. Soc. 2002, 124, 8891.
21. (b) Tanaka, T.; Matsumoto, A. J. Am. Chem. Soc. 2002, 124, 9676.
22. (c) Polymerization in organized Media; Paleos, C. M., Ed.; Gordon and Breach: Philadelphia, 1992.
23. (d) Nomura, S.; Itoh, T.; Nakasho, H.; Uno, T.; Kubo, M.; Sada, K.; Inoue, K.; Miyata, M. J. Am. Chem. Soc. 2004, 126, 2035.
24. (e) Ouyang, X.; Fowler, F. K.; Lauher, J. W. J. Am. Chem. Soc. 2003, 125, 12400.
25. (a) Sukenik, C. N.; Bonapace, J. A. P.; Mandel, N. S.; Lau, P.-Y.; Wood, G.; Bergman, R. G. J. Am. Chem. Soc. 1977, 99, 851.
26. (b) Dessolin, M.; Eisenstein, O.; Golfier, M.; Prange, T.; Sautet, P. J. Chem. Soc., Chem. Commun. 1992, 132.
27. (c) Smrcina, M.; Vyskocil, S.; Hanus, V.; Polasek, M.; Langer, V.; Chew, B. G. M.; Zax, D. B.; Verrier, H.; Harper, K.; Claxton, T. A.; Kocovsky, P. J. Am. Chem. Soc. 1996, 118, 487.
28. (d) Elizabe, L.; Kariuki, B. M.; Harris, K. D. M.; Tremayne, M.; Epple, M.; Thomas, J. M. J. Phys. Chem. B 1997, 101, 8827.
29. (a) Ohashi, Y.; Yanagi, K.; Kurihara, T.; Sasada, Y.; Ohgo, Y. J. Am. Chem. Soc. 1982, 104, 6353.
30. (b) Ohashi, Y.; Yanagi, K.; Kurihara, T.; Sasada, Y.; Ohgo, Y. J. Am. Chem. Soc. 1981, 103, 5805.
31. (c) Ohashi, Y. Acc. Chem. Res. 1988, 21, 268.
32. Praveen, T.; Samanta, U.; Das, T.; Shashidhar, M. S.; Chakrabarti, P. J. Am. Chem. Soc. 1998, 120, 3842.
33. Nery, J. G.; Bolbach, G.; Isabelle, W.; Lahav, M. Angew Chem., Int. Ed. 2003, 42, 2157.
34. Chung, S.-K.; Ryu, Y. Carbohydr. Res. 1994, 258, 145.
35. Powder XRD studies were also in agreement with a crystal-to-crystal transformation (see Supporting Information).
36. N2 reactions are 3.42 Å/147°,5a 2.9 Å/164°,5b 3.20 Å/173°,5c and 4.61 Å/168°.5d