Synthesis of 5,5'-bicalix[6]arene and 5,5'-bicalix[8]arene systems

Journal of Organic Chemistry

Volumn 64, Issue 21, 1999, Pages 8018-8020

  Bottino, Alessandra ^a   Cunsolo, Francesca ^a   Piattelli, Mario ^a   Garozzo, Domenico ^a   Neri, Placido ^b  

^a CNR   (Italy)

^b UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; COMPUTER MODEL; CONFORMATION; MOLECULAR MODEL; OXIDATION; SYNTHESIS;

EID: 0032747924     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9905017     Document Type: Article

References (25)

1. Lehn, J. M. Supramolecular Chemistry, Concepts and Perspectives; VCH: Weinheim, 1995.
2. For comprehensive reviews on calixarenes see: Calixarenes, a Versatile Class of Macrocydic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, The Netherlands, 1991. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713. Gutsche, C. D. Calixarenes Revisited; The Royal Society of Chemistry: Cambridge, 1998.
3. For comprehensive reviews on calixarenes see: Calixarenes, a Versatile Class of Macrocydic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, The Netherlands, 1991. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713. Gutsche, C. D. Calixarenes Revisited; The Royal Society of Chemistry: Cambridge, 1998.
4. For comprehensive reviews on calixarenes see: Calixarenes, a Versatile Class of Macrocydic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, The Netherlands, 1991. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713. Gutsche, C. D. Calixarenes Revisited; The Royal Society of Chemistry: Cambridge, 1998.
5. For comprehensive reviews on calixarenes see: Calixarenes, a Versatile Class of Macrocydic Compounds; Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, The Netherlands, 1991. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. Ikeda, A.; Shinkai, S. Chem. Rev. 1997, 97, 1713. Gutsche, C. D. Calixarenes Revisited; The Royal Society of Chemistry: Cambridge, 1998.
6. Asfari, Z.; Weiss, J.; Vicens, J. Synlett 1993, 719.
7. Wasikievicz, W.; Rokicki, G.; Kielkiewicz, J.; Böhmer, V. Angew. Chem., Int. Ed. Engl. 1994, 33, 214. See also literature cited in ref 7.
8. Akimura, T.; Matsumoto, S.; Teshima, O.; Nagasaki, T.; Shinkai, S. Tetrahedron Lett. 1991, 32, 5111.
9. Aleksiuk, O.; Biali, S. E. J. Org. Chem. 1996, 61, 5670.
10. Neri, P.; Bottino, A.; Cunsolo, F.; Piattelli, M.; Gavuzzo, E. Angew. Chem., Int. Ed. 1998, 37, 166.
11. For a preliminary report on the O-alkylation of 5,5′-bicalix[4]-arene see: Bottino, A.; Cunsolo, F.; Piattelli, M.; Neri, P. Tetrahedron Lett. 1998, 39, 9549.
12. Under similar conditions Gutsche and co-workers have isolated hexabenzoyl-p-H-calix[6]arene (Gutsche, C. D.; Lin, L.-g. Tetrahedron 1986, 42, 1633), while in the presence of NaH, the tetrabenzoyl derivative was obtained (Rogers, J. S.; Gutsche, C. D. J. Org. Chem. 1992, 57, 3152).
13. Under similar conditions Gutsche and co-workers have isolated hexabenzoyl-p-H-calix[6]arene (Gutsche, C. D.; Lin, L.-g. Tetrahedron 1986, 42, 1633), while in the presence of NaH, the tetrabenzoyl derivative was obtained (Rogers, J. S.; Gutsche, C. D. J. Org. Chem. 1992, 57, 3152).
14. The complete IUPAC name for this compound is 5,5′-bicalix-[6]arene-37,37′,38,38′,39,39′,40,40′, 41,41′,42,42′-dodecaol.
15. Gutsche, C. D.; Bauer, L. J. J. Am. Chem. Soc. 1985, 107, 6052.
16. Consoli, G. M. L.; Cunsolo, F.; Piattelli, M.; Neri, P. J. Org. Chem. 1996, 61, 2195.
17. For examples of selective trans-de-tert-butylation in smaller calixarenes see: van Loon, J. D.; Arduini, A.; Coppi, L.; Verboom, W.; Pochini, A.; Ungaro, R.; Harkema, S. and Reinhoudt, D. N. J. Org. Chem. 1990, 55, 5639. See, K. A.; Fronczek, F. R.; Watson, W. H.; Kaahyap, R. P.; Gutsche, C. D. J. Org. Chem. 1991, 56, 7256. de Mendoza, J.; Carramolino, M.; Cuevas, F.; Nieto, P. M.; Prados, P.; Reinhoudt, D. N.; Verboom, W.; Ungaro, R.; Casnati, A. Synthesis 1994, 47.
18. For examples of selective trans-de-tert-butylation in smaller calixarenes see: van Loon, J. D.; Arduini, A.; Coppi, L.; Verboom, W.; Pochini, A.; Ungaro, R.; Harkema, S. and Reinhoudt, D. N. J. Org. Chem. 1990, 55, 5639. See, K. A.; Fronczek, F. R.; Watson, W. H.; Kaahyap, R. P.; Gutsche, C. D. J. Org. Chem. 1991, 56, 7256. de Mendoza, J.; Carramolino, M.; Cuevas, F.; Nieto, P. M.; Prados, P.; Reinhoudt, D. N.; Verboom, W.; Ungaro, R.; Casnati, A. Synthesis 1994, 47.
19. For examples of selective trans-de-tert-butylation in smaller calixarenes see: van Loon, J. D.; Arduini, A.; Coppi, L.; Verboom, W.; Pochini, A.; Ungaro, R.; Harkema, S. and Reinhoudt, D. N. J. Org. Chem. 1990, 55, 5639. See, K. A.; Fronczek, F. R.; Watson, W. H.; Kaahyap, R. P.; Gutsche, C. D. J. Org. Chem. 1991, 56, 7256. de Mendoza, J.; Carramolino, M.; Cuevas, F.; Nieto, P. M.; Prados, P.; Reinhoudt, D. N.; Verboom, W.; Ungaro, R.; Casnati, A. Synthesis 1994, 47.
20. An example of calix[8]arene selectively functionalized at the upper rim was recently obtained by condensation of fragments already bearing different functions: Tsue, H.; Ohmori, M.; Hirao, K. J. Org. Chem. 1998, 63, 4866.
21. The complete IUPAC name for this compound is 11,11′,17,17′,-23,23′,29,29′,35,35′,41,41′, 47,47′-tetradeca-tert-butyl-5,5′-bicalix[8]arene-49,49′,50, 50′,51,51′,52,52′,53,53′,54,54′,55,55′,56, 56′-hexadecaol.
22. Energies were evaluated with the MM3 force field with GB/SA chloroform-model-solvent as implemented in the program Macro-Model V4.5: Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Liskamp, R.; Lipton, M.; Caufield, C.; Chang, G.; Hendrickson, T.; Still, W. C. J. Comput. Chem. 1990, 11, 440.
23. Molins, M. A.; Nieto, P. M.; Sanchez, C.; Prados, P.; de Mendoza, J.; Pons, M. J. Org. Chem. 1992, 57, 6924. van Hoorn, W. P.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 7180.
24. Molins, M. A.; Nieto, P. M.; Sanchez, C.; Prados, P.; de Mendoza, J.; Pons, M. J. Org. Chem. 1992, 57, 6924. van Hoorn, W. P.; van Veggel, F. C. J. M.; Reinhoudt, D. N. J. Org. Chem. 1996, 61, 7180.
25. Gutsche, C. D.; Gutsche, A. E.; Karaulov, A. I. J. Incl. Phenom. 1885, 3, 447.