Syntheses of inherently chiral monosulfinyltrithiacalix[4]arenes by the oxidation of one of the bridging sulfurs of a tetrathiacalix[4]arene fixed in the 1,3-alternate conformation

Israel Journal of Chemistry

Volumn 41, Issue 4, 2001, Pages 303-308

  Morohashi, Naoya ^a   Naito, Ryoichiro ^a   Iki, Nobuhiko ^a   Miyano, Sotaro ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0040486984     PISSN: 00212148     EISSN: None     Source Type: Journal    
DOI: 10.1560/VQJK-0Q49-HRWR-E2F1     Document Type: Article

References (21)

1. (a) Gutsche, C.D. In Calixarenes, Monographs in Supramolecular Chemistry; Stoddart, J.F., Ed.; The Royal Society of Chemistry: Cambridge, 1989.
2. (b) Calixarenes - A Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V.; Eds.; Kluwer Academic Publishers: Dordrecht, 1991.
3. (c) Gutsche, C.D. Calixarenes Revisited, Monographs in Supramotecutar Chemistry; Stoddart, J.F., Ed.; The Royal Society of Chemistry. Cambridge, 1998.
4. (d) Calixarenes 2001; Asfari, Z.; Böhmer, V.; Harrowfield, J.M.; Vicens, J.; Eds.; Kluwer Academic Publishers; Dordrecht, 2001.
5. Kubo, Y.; Maeda, S.; Tokita, S.; Kubo, M. Nature 1996, 382, 522-524.
6. Araki, K.; Inada, K.; Shinkai, S. Angew. Client., Int. Ed. Engl. 1996, 35, 72-74.
7. See, for example: (a) Arimura, T.: Kawabata, H.; Matsuda, T.; Muramatsu, T.; Satoh, H.; Fujio, K; Manabe, O.; Shinkai, S. J. Org. Chem. 1991, 56, 301-306.
8. (b) Marra, A.; Scherrmann, M-C.; Dondoni, A.; Casnati, A.; Minari, P.; Ungaro, R. Angew, Client., Int. Ed. Engl. 1994, 33, 2479-2481.
9. See, for example: (a) Iwamoto, K.; Shimizu, H.; Araki, K.; Shinkai, S. J. Am. Chem. Soc. 1993, 115, 3997-4006.
10. (b) Caccamese, S.; Notti, A.; Pappalardo, S.; Parisi, M.F.; Principato, G. Tetrahedron 1999, 55. 5505-5514.
11. Kumagai, H.; Hasegawa, M.; Miyanari, S.; Sugawa, Y.; Sato, Y.; Hori, T.; Ueda, S.; Kamiyama. H.; Miyano, S. Tetrahedron Lett. 1997, 38, 3971-3972.
12. Iki, N.; Horiuchi, T.; Oka, H.; Koyama, K.; Morohashi, N.; Kabuto, C.; Miyano, S. J. Chem. Soc., Pekin Trans. 2 2001, 2219-2225.
13. Morohashi, N.; Iki, N.; Sugawara, A.; Miyano, S. Tetrahedron 2001, 57, 5557-5563.
14. Morohashi, N.; Iki, N.; Onodera. T.; Kabuto. C.; Miyano, S. Tetrahedron Lett. 2001, 41, 5093-5097.
15. Araki, K.; Iwamoto, K.: Shinkai, S.; Matsuda, T. Chem. Lett. 1989, 1747-1750.
16. See, for example: (a) Iwamoto, K.; Araki, K.: Shinkai, S. Tetrahedron 1991, 47, 4325-4342.
17. (b) Gutsche, C. D.; Reddy, P.A. J. Org. Chem. 1991, 56, 4783-4791.
18. Lhoták, P. Tetrahedron 2001, 57, 4775-4779.
19. Iki, N.; Narumi, F.; Fujimoto, T.; Morohashi, N.; Miyano, S. J. Chem. Soc., Perkin Trans. 2 1998, 2745-2750.
20. Iki, N.; Morohashi, N.; Narumi, F.: Fujimoto, T.; Suzuki, T.; Miyano, S. Tetrahedron Lett. 1999, 40, 7337-7341.
21. A similar spectrum (two doublets for the aromatic protons) was observed for a chiral calixarene derivative existing in the 1,3-alternate conformation. See: Neri, P.; Bottino, A.; Geraci, C.; Piattelli, M. Tetrahedron: Asymmetry 1996, 7, 17-20.