Structure and equilibration studies of bis- and tris(spirodienone) derivatives of medium-sized calixarenes

Journal of Organic Chemistry

Volumn 61, Issue 26, 1996, Pages 9512-9521

  Grynszpan, Flavio ^a   Biali, Silvio E ^a  

^a HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000615310     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961358+     Document Type: Article

References (31)

1. For reviews on calixarenes see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. (b) Gutsche, C. D. In Synthesis of Macrocycles: Design of Selective Completing Agents; Izatt, R. M., Christensen, J. J., Eds.; Wiley: New York, 1987; p 93. (c) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (d) Gutsche, C. D. Aldrichim. Acta, 1995, 28, 1. (e) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
2. For reviews on calixarenes see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. (b) Gutsche, C. D. In Synthesis of Macrocycles: Design of Selective Completing Agents; Izatt, R. M., Christensen, J. J., Eds.; Wiley: New York, 1987; p 93. (c) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (d) Gutsche, C. D. Aldrichim. Acta, 1995, 28, 1. (e) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
3. For reviews on calixarenes see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. (b) Gutsche, C. D. In Synthesis of Macrocycles: Design of Selective Completing Agents; Izatt, R. M., Christensen, J. J., Eds.; Wiley: New York, 1987; p 93. (c) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (d) Gutsche, C. D. Aldrichim. Acta, 1995, 28, 1. (e) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
4. For reviews on calixarenes see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. (b) Gutsche, C. D. In Synthesis of Macrocycles: Design of Selective Completing Agents; Izatt, R. M., Christensen, J. J., Eds.; Wiley: New York, 1987; p 93. (c) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (d) Gutsche, C. D. Aldrichim. Acta, 1995, 28, 1. (e) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
5. For reviews on calixarenes see: (a) Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989. (b) Gutsche, C. D. In Synthesis of Macrocycles: Design of Selective Completing Agents; Izatt, R. M., Christensen, J. J., Eds.; Wiley: New York, 1987; p 93. (c) Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. (d) Gutsche, C. D. Aldrichim. Acta, 1995, 28, 1. (e) Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
6. For a review on calixarene spirodienone derivatives see: Aleksiuk, O.; Grynszpan, F.; Litwak, A. M.; Biali, S. E. New J. Chem. 1996, 20, 476. For a review on spirodienone derivatives of bis-(naphthols) see: Ward, R. S. Chem. Br. 1973, 9, 44.
7. For a review on calixarene spirodienone derivatives see: Aleksiuk, O.; Grynszpan, F.; Litwak, A. M.; Biali, S. E. New J. Chem. 1996, 20, 476. For a review on spirodienone derivatives of bis-(naphthols) see: Ward, R. S. Chem. Br. 1973, 9, 44.
8. (a) Litwak, A. M.; Grynszpan, F.; Aleksiuk, O.; Cohen, S.; Biali, S. E. J. Org. Chem. 1993, 58, 393.
9. (b) Aleksiuk, O.; Grynszpan, F.; Biali, S. E. J. Chem. Soc., Chem. Commun. 1993, 11.
10. (c) Aleksiuk, O.; Grynszpan, F.; Biali, S. E. J. Org. Chem. 1993, 58, 1994.
11. (d) Grynszpan, F.; Aleksiuk, O.; Biali, S. E. J. Org. Chem. 1994, 59, 2070.
12. (e) Aleksiuk, O.; Grynszpan, F.; Biali, S. E. J. Incl. Phenom. 1994, 19, 237.
13. For recent studies on spironaphthalenones see: Kasturi, T. R.; Jayaram, S. K.; Pragnacharyulu, P. V. P.; Sattigeri, J. A.; Reddy, G. M.; Kumar, K. A. Tetrahedron, 1993, 49, 113. Kasturi, T. R.; Kumar, K. A.; Pragnacharyulu, P. V. P. Tetrahedron, 1993, 49, 125. Kasturi, T. R.; Kumar, K. A.; Pragnacharyulu, P. V. P.; Srivedi, G. Tetrahedron, 1993, 49, 135.
14. For recent studies on spironaphthalenones see: Kasturi, T. R.; Jayaram, S. K.; Pragnacharyulu, P. V. P.; Sattigeri, J. A.; Reddy, G. M.; Kumar, K. A. Tetrahedron, 1993, 49, 113. Kasturi, T. R.; Kumar, K. A.; Pragnacharyulu, P. V. P. Tetrahedron, 1993, 49, 125. Kasturi, T. R.; Kumar, K. A.; Pragnacharyulu, P. V. P.; Srivedi, G. Tetrahedron, 1993, 49, 135.
15. For recent studies on spironaphthalenones see: Kasturi, T. R.; Jayaram, S. K.; Pragnacharyulu, P. V. P.; Sattigeri, J. A.; Reddy, G. M.; Kumar, K. A. Tetrahedron, 1993, 49, 113. Kasturi, T. R.; Kumar, K. A.; Pragnacharyulu, P. V. P. Tetrahedron, 1993, 49, 125. Kasturi, T. R.; Kumar, K. A.; Pragnacharyulu, P. V. P.; Srivedi, G. Tetrahedron, 1993, 49, 135.
16. Aleksiuk, O.; Cohen, S.; Biali, S. E. J. Am. Chem. Soc. 1995, 117, 9645.
17. For a preliminary communication see: Grynszpan, F.; Biali, S. E. J. Chem. Soc., Chem. Commun. 1994, 2545. Part of this work was presented in the XXth International Symposium on Macrocyclic Chemistry, Jerusalem, Israel, July 2-7, 1995, Abstract, p 3. Grynszpan, F.; Aleksiuk, O.; Biali, S. E. Pure Appl. Chem. 1996, 68, 1429.
18. For a preliminary communication see: Grynszpan, F.; Biali, S. E. J. Chem. Soc., Chem. Commun. 1994, 2545. Part of this work was presented in the XXth International Symposium on Macrocyclic Chemistry, Jerusalem, Israel, July 2-7, 1995, Abstract, p 3. Grynszpan, F.; Aleksiuk, O.; Biali, S. E. Pure Appl. Chem. 1996, 68, 1429.
19. Mislow, K. Chimia, 1986, 40, 395.
20. Biali, S. E.; Buda, A. M.; Mislow, K. J. Org. Chem. 1988, 53, 1289.
21. Siegel, J.; Anet, F. A. L. J. Org. Chem. 1988, 53, 2629.
22. The cavity radius was calculated from the O⋯O nonbonded distances and the van der Waals oxygen radius (2.0 Å) (Gordon, A. J.; Ford, R. A. The Chemist's Companion; Wiley: New York, 1972; p 109).
23. Adams, R.; Johnson, J. R.; Wilcox, C. F., Jr. Laboratory Experiments in Organic Chemistry; Macmillan: New York, 1972; p 109.
24. The exchange rates at the coalescence temperatures were calculated from the Av values according to: Gutowsky, H. S.; Holm, C. H. J. Phys. Chem. 1956, 25, 1228.
25. c is dependent of the chemical shift difference between the exchanging signals at T. For a discussion of the lineshape changes in temperature dependent NMR spectra see: Kessler, H. Angew. Chem., Int. Ed. Engl. 1970, 9, 219.
26. Still, W. C.; Mohamadi, F.; Richards, N. J. G.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T. MACROMODEL V3.0, Department of Chemistry, Columbia University, New York.
27. The crystallographic structure of 9 is described in reference 6.
28. This combination was previously used for the oxidation of bis-(naphthols) to their corresponding spirodienone derivatives. See: Bennett, D. J.; Dean, F. M.; Herbin, G. A.; Matkin, D. A.; Price, A. W. J. Chem. Soc., Perkin Trans. 1 1980, 1978.
29. Prelog, V.; Gerlach, H. Helv. Chim. Acta 1964, 47, 2288. Prelog, V. Science 1976, 17, 193.
30. Prelog, V.; Gerlach, H. Helv. Chim. Acta 1964, 47, 2288. Prelog, V. Science 1976, 17, 193.
31. Singh, M. D.; Siegel, J.; Biali, S. E.; Mislow, K. J. Am. Chem. Soc. 1987, 109, 3397.