Preparation and conformation of monohalotetrahydroxycalix[5]arenes

Journal of Organic Chemistry

Volumn 61, Issue 24, 1996, Pages 8419-8424

  Van Gelder, Joel M ^a   Aleksiuk, Oleg ^a   Biali, Silvio E ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001712309     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9611428     Document Type: Article

References (38)

1. For reviews on calixarenes, see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. (d) Gutsche, C. D. Aldrichimica Acta 1995, 28, 1.
2. For reviews on calixarenes, see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. (d) Gutsche, C. D. Aldrichimica Acta 1995, 28, 1.
3. For reviews on calixarenes, see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. (d) Gutsche, C. D. Aldrichimica Acta 1995, 28, 1.
4. For reviews on calixarenes, see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. (b) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (c) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. (d) Gutsche, C. D. Aldrichimica Acta 1995, 28, 1.
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11. (g) Matsuda, K.; Nakamura, N.; Takahashi, K.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1995, 117, 5550. For additional synthesis of dehydroxylated calixarenes, see: Fukazawa, Y.; Demaya, K.; Usui, S. Tetrahedron Lett. 1992, 33, 5803. Usui, S.; Deyama, K.; Kinoshita, R.; Odagaki, Y.; Fukazawa, Y. Tetrahedron Lett. 1993, 34, 8127; Rajca, A.; Padmakumar, R.; Smithisler, D. J.; Desai, S. R.; Ross, C. R., II; Stezowski, J. J. J. Org. Chem. 1994, 59, 7701.
12. (g) Matsuda, K.; Nakamura, N.; Takahashi, K.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1995, 117, 5550. For additional synthesis of dehydroxylated calixarenes, see: Fukazawa, Y.; Demaya, K.; Usui, S. Tetrahedron Lett. 1992, 33, 5803. Usui, S.; Deyama, K.; Kinoshita, R.; Odagaki, Y.; Fukazawa, Y. Tetrahedron Lett. 1993, 34, 8127; Rajca, A.; Padmakumar, R.; Smithisler, D. J.; Desai, S. R.; Ross, C. R., II; Stezowski, J. J. J. Org. Chem. 1994, 59, 7701.
13. (g) Matsuda, K.; Nakamura, N.; Takahashi, K.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1995, 117, 5550. For additional synthesis of dehydroxylated calixarenes, see: Fukazawa, Y.; Demaya, K.; Usui, S. Tetrahedron Lett. 1992, 33, 5803. Usui, S.; Deyama, K.; Kinoshita, R.; Odagaki, Y.; Fukazawa, Y. Tetrahedron Lett. 1993, 34, 8127; Rajca, A.; Padmakumar, R.; Smithisler, D. J.; Desai, S. R.; Ross, C. R., II; Stezowski, J. J. J. Org. Chem. 1994, 59, 7701.
14. (g) Matsuda, K.; Nakamura, N.; Takahashi, K.; Inoue, K.; Koga, N.; Iwamura, H. J. Am. Chem. Soc. 1995, 117, 5550. For additional synthesis of dehydroxylated calixarenes, see: Fukazawa, Y.; Demaya, K.; Usui, S. Tetrahedron Lett. 1992, 33, 5803. Usui, S.; Deyama, K.; Kinoshita, R.; Odagaki, Y.; Fukazawa, Y. Tetrahedron Lett. 1993, 34, 8127; Rajca, A.; Padmakumar, R.; Smithisler, D. J.; Desai, S. R.; Ross, C. R., II; Stezowski, J. J. J. Org. Chem. 1994, 59, 7701.
15. (a) Gibbs, C. G.; Gutsche, C. D. J. Am. Chem. Soc. 1993, 115, 5338.
16. (b) Ting, Y.; Verboom, W.; Groenen, L. C.; van Loon, J. D.; Reinhoudt, D. N. J. Chem. Soc., Chem. Commun. 1990, 1435.
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18. (d) Delaigue, X.; Hosseini, M. W.; Kyritsakas, N.; de Cian, A.; Fischer, J. J. Chem. Soc., Chem. Commun. 1995, 609.
19. (e) Gibbs, C. G.; Sujeeth, P. K.; Rogers, J. S.; Stanley, G. G.; Krawiec, M.; Watson, W. H.; Gutsche, C. D. J. Org. Chem. 1995, 60, 8394.
20. (a) Ohseto, F.; Murakami, H.; Araki, K.; Shinkai, S. Tetrahedron Lett, 1992, 33, 1217.
21. (b) Aleksiuk, O.; Grynszpan, F.; Biali, S. E. J. Org. Chem. 1993, 58, 1994.
22. (c) Grynszpan, F.; Aleksiuk, O.; Biali, S. E. J. Org. Chem., 1994, 59, 2070.
23. (d) Aleksiuk, O.; Cohen, S.; Biali, S. E. J. Am. Chem. Soc. 1995, 117, 9645.
24. For a review on spirodienone calixarene derivatives, see: Aleksiuk, O.; Grynszpan, F.; Litwak, M. A.; Biali, S. E. New J. Chem. 1996, 20, 473.
25. For reviews on diazonium derivatives, see: The Chemistry of Diazonium and Diazo Groups; Patai, S., Ed.; Wiley: Chichester, 1978.
26. For a recent review on the chemistry of calix[5]arenes, see: Asfari, Z.; Vicens, J. Acros Org. Acta 1995, 1, 18.
27. (a) For a review on dediazoniations, see: Zollinger, H. In The Chemistry of Functional Groups, Supplement C, Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 15.
28. (b) For a review on aliphatic diazonium ions, see: Kirmse, W. Angew. Chem., Int. Ed. Engl. 1976, 15, 251.
29. For a recent work on the conformation and inversion barriers of derivatives of p-tert-butylcalix[5]arene, see: Stewart, D. R.; Krawiec, M.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. J. Am. Chem. Soc. 1995, 117, 586.
30. For other examples of formation of chlorobenzenes by abstraction of a chlorine atom from the solvent, see: Oae, S.; Shinhama, K.; Kim, Y. H. Bull. Chem. Soc. Jpn. 1980, 2023.
31. Wulfman, D. S. In ref 6; Chapter 8. See p 278 and references therein.
32. Fluoride ion in an aprotic solvent may behave as a strong base. See, for example: Hoz, S.; Albeck, M.; Rappoport, Z. Synthesis 1975, 162. Bartsch, R. A. J. Org. Chem. 1970, 35, 1023.
33. Fluoride ion in an aprotic solvent may behave as a strong base. See, for example: Hoz, S.; Albeck, M.; Rappoport, Z. Synthesis 1975, 162. Bartsch, R. A. J. Org. Chem. 1970, 35, 1023.
34. The authors have deposited atomic coordinates for the structures with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, U.K.
35. Dumas, J.-M.; Gomerl, M.; Guerin, M. In Supplement D: The chemistry of halides, pseudohalides and azides; Patai, S., Rappoport, Z., Eds.; Wiley: Chichester, 1983; Chapter 21, pp 989-991.
36. The barriers were calculated from the exchange rates at the coalescence temperatures calculated according to the following: Gutowsky, H. S.; Holm, C. H. J. Chem. Phys. 1956, 25, 1228.
37. Gutsche, C. D.; Bauer, L. J. J. Am. Chem. Soc. 1985, 107, 6052.
38. The shock sensitivity of diazonium salts can be reduced by complexation with crown ethers (Sheppard, W. A.; Gokel, G. W.; Webster, O. W.; Betterton, K.; Timberlake, J. W. J. Org. Chem. 1979, 44, 1717.) It is not known at present whether the neighboring OH groups exert a similar effect.