Easy and selective method for the synthesis of various mono-O- functionalized Calix[4]arenes: De-O-functionalization using TiCl4

Journal of Organic Chemistry

Volumn 75, Issue 22, 2010, Pages 7550-7558

  Bois, Joackim ^a   Espinas, Jeff ^a,b   Darbost, Ulrich ^a   Felix, Caroline ^a   Duchamp, Christian ^a   Bouchu, Denis ^a   Taoufik, Mostafa ^b   Bonnamour, Isabelle ^a  

^a UNIVERSITÉ LYON 1   (France)

^b UNIVERSITÉ LYON 1   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUNDS; CHLORINE COMPOUNDS; SYNTHESIS (CHEMICAL);

CALIX[4]ARENES; FUNCTIONALIZATIONS; FUNCTIONALIZED; P-TERT-BUTYLCALIX[4]ARENE; REACTION MECHANISM; TITANIUM DICHLORIDE; TITANIUM TETRACHLORIDES;

TITANIUM COMPOUNDS;

2 METHYLPROPYLOXY; 26,27,28 TRIHYDROXY 25 (3 CYANOPROPYLOXY)CALIX [4]ARENE; 3 BUTYNYLOXY; 3 CYANOPROPYLOXY; 3 ETHOXYCARBONYLPROPYLOXY; 3 HYDROXYPROPYLOXY; 4 BROMOBUTYLOXY; 4 TERT BUTYLCALIX[4]ARENE; 5,11,17,23 TETRA TERT BUTYL 25 CYANOMETHYLOXY 26,27,28 TRIHYDROXYCALIX[4]ARENE; 5,11,17,23 TETRA TERT BUTYL 25 ETHOXYCARBONYLMETHYLOXY 26,27,28 TRIHYDROXYCALIX[4]ARENE; 5,11,17,23 TETRA TERT BUTYL 25 PROPYLOXY 26,27,28 TRIHYDROXYCALIX[4]ARENE; 5,11,17,23 TETRA TERT BUTYL 25,26 BIS(BUT 3 YNYLOXY) 27,28 DIHYDROXYCALIX[4]ARENE; 5,11,17,23 TETRA TERT BUTYL 25,27 DIOXO 26,28 DI (3 ETHOXYCARBONYLPROPYLOXY)CALIX[4]ARENE TITANIUM DICHLORIDE; 5,11,17,23 TETRA TERT BUTYL 26,27,28 TRIHYDROXY 25 (3 BUTYNYLOXY)CALIX[4]ARENE; 5,11,17,23 TETRA TERT BUTYL 26,27,28 TRIHYDROXY 25 (3 CYANOPROPYLOXY)CALIX[4]ARENE; 5,11,17,23 TETRA TERT BUTYL 26,27,28 TRIHYDROXY 25 (3 ETHOXYCARBONYLPROPYLOXY) CALIX[4]ARENE; 5,11,17,23 TETRA TERT BUTYL 26,27,28 TRIHYDROXY 25 (3 ETHOXYCARBONYLPROPYLOXY)CALIX[4]ARENE; 5,11,17,23 TETRA TERT BUTYL 26,27,28 TRIHYDROXY 25 (3 HYDROXYPROPYLOXY)CALIX[4]ARENE; 5,11,17,23 TETRA TERT BUTYL 26,27,28 TRIHYDROXY 25 (4 BROMOBUTYLOXY)CALIX[4]ARENE; 5,11,17,23 TETRA TERT BUTYL 26,27,28 TRIHYDROXY25 (2 METHYLPROPYLOXY)CALIX[4]ARENE; BUTYRIC ACID; CALIX[4]ARENE DERIVATIVE; CYANOMETHYLOXY; ETHOXYCARBONYLMETHYLOXY; ETHYL 4 CHLOROBUTYRATE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; PROPYLOXY; TITANIUM TETRACHLORIDE; TITANOCENE DICHLORIDE; TRIOXOCALIX[4]ARENE TITANIUM DICHLORIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GAS CHROMATOGRAPHY; HYDROLYSIS; ISOLATION PROCEDURE; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; SYNTHESIS;

EID: 78449265384     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101319s     Document Type: Article

References (38)

1. Mandolini, L., Ungaro, R., Eds. Calixarenes in Action; Imperial College Press: London, 2000.
2. Asfari, Z., Bohmer, V., Harrowfield, J., Vicens, J., Eds. Calixarenes 2001; Kluwer: Dordrecht, The Netherlands, 2001.
3. Gutsche, C. D., Ed. Calixarenes: An Introduction, 2 nd ed.; Royal Society of Chemistry: London, 2008.
4. Tabakci, M.; Memon, S.; Yilmaz, M. Tetrahedron 2007, 63, 6861-6865
5. Boyko, V. I.; Yakovenko, A. V.; Matvieiev, Y. I.; Kalchenko, O. I.; Shishkin, O. V.; Shishkina, S. V.; Kalchenko, V. I. Tetrahedron 2008, 64, 7567-7573
6. Bois, J.; Bonnamour, I.; Duchamp, C.; Parrot-Lopez, H.; Darbost, U.; Felix, C. New J. Chem. 2009, 33, 2128-2135
7. Boyko, V. I.; Matvieiev, Y. I.; Klyachina, M. A.; Yesypenko, O. A.; Shishkina, S. V.; Shishkin, O. V.; Kalchenko, V. I. Tetrahedron 2009, 65, 4220-4227
8. Da Silva, E.; Memmi, L.; Coleman, A. W.; Rather, B.; Zaworotko, M. J. J. Supramol. Chem. 2002, 1, 135-138
9. Collins, E. M.; McKervey, M. A.; Madigan, E.; Moran, M. B.; Owens, M.; Ferguson, G.; Harris, S. J. J. Chem. Soc., Perkin Trans. 1 1991, 3137-3142
10. Sun, J.; Liu, D. M.; Wang, J. X.; Yan, C. G. J. Inclusion Phenom. Macrocyclic Chem. 2009, 64, 317-324
11. Zhang, W. C.; Huang, Z. T. Synthesis 1997, 1073-1076
12. Chawla, H. M.; Pant, N.; Srivastava, B. Tetrahedron Lett. 2005, 46, 7259-7262
13. Chen, X.; Dings, R. P. M.; Nesmelova, I.; Debbert, S.; Haseman, J. R.; Maxwell, J.; Hoye, T. R.; Mayo, K. H. J. Med. Chem. 2006, 49, 7754-7765
14. Creaven, B. S.; Gernon, T. L.; McGinley, J.; Moore, A.-M.; Toftlund, H. Tetrahedron 2006, 62, 9066-9071
15. Li, Z.-T.; Ji, G.-Z.; Zhao, C.-X.; Yuan, S.-D.; Ding, H.; Huang, C.; Du, A.-L.; Wei, M. J. Org. Chem. 1999, 64, 3572-3584
16. Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815-7820
17. Yakovenko, A. V.; Boyko, V. I.; Kalchenko, V. I.; Baldini, L.; Casnati, A.; Sansone, F.; Ungaro, R. J. Org. Chem. 2007, 72, 3223-3231
18. Halouani, H.; Dumazet-Bonnamour, I.; Perrin, M.; Lamartine, R. J. Org. Chem. 2004, 69, 6521-6527
19. Hosseini, A.; Taylor, S.; Accorsi, G.; Armaroli, N.; Reed, C. A.; Boyd, P. D. W. J. Am. Chem. Soc. 2006, 128, 15903-15913
20. Kenis, P. J. A.; Noordman, O. F. J.; Schonherr, H.; Kerver, E. G.; Snellink-Ruel, B. H. M.; van Hummel, G. J.; Harkema, S.; van der Vorst, C. P. J. M.; Hare, J.; Picken, S. J.; Engbersen, J. F. J.; van Hulst, N. F.; Vancso, G. J.; Reinhoudt, D. N. Chem.-Eur. J. 1998, 4, 1225-1234
21. Da Silva, E.; Coleman, A. W. Tetrahedron 2003, 59, 7357-7364
22. Alekseeva, E. A.; Mazepa, A. V.; Gren, A. I. Russ. J. Gen. Chem. 2001, 71, 1786-1792
23. Shu, C.-M.; Chung, W.-S.; Wu, S.-H.; Ho, Z.-C.; Lin, L.-G. J. Org. Chem. 1999, 64, 2673-2679
24. Arnaud-Neu, F.; Caccamese, S.; Fuangswasdi, S.; Pappalardo, S.; Parisi, M. F.; Petringa, A.; Principato, G. J. Org. Chem. 1997, 62, 8041-8048
25. Iwamoto, K.; Araki, K.; Shinkai, S. Tetrahedron 1991, 47, 4325-4342
26. Groenen, L. C.; Ruel, B. H. M.; Casnati, A.; Verboom, W.; Pochini, A.; Ungaro, R.; Reinhoudt, D. N. Tetrahedron 1991, 47, 8379-8384
27. Shang, S.; Khasnis, D. V.; Burton, J. M.; Santini, C. J.; Fan, M.; Small, A. C.; Lattman, M. Organometallics 1994, 13, 5157-5159
28. Casnati, A.; Arduini, A.; Ghidini, E.; Pochini, A.; Ungaro, R. Tetrahedron 1991, 47, 2221-2228
29. Matvieiev, Y. I.; Boyko, V. I.; Podoprigorina, A. A.; Kalchenko, V. I. J. Inclusion Phenom. Macrocyclic Chem. 2008, 61, 89-92
30. Floriani, C.; Floriani-Moro, R. Adv. Organomet. Chem. 2001, 47, 167-233
31. Zanotti-Gerosa, A.; Solari, E.; Giannini, L.; Floriani, C.; Re, N.; Chiesi-Villa, A.; Rizzoli, C. Inorg. Chim. Acta 1998, 270, 298-311
32. Friedrich, A.; Radius, U. Eur. J. Inorg. Chem. 2004, 4300-4316
33. Santoyo-Gonzalez, F.; Torres-Pinedo, A.; Sanchez-Ortega, A. J. Org. Chem. 2000, 65, 4409-4414
34. Gong, S.; Wang, W.; Chen, Y.; Meng, L.; Wan, T. New J. Chem. 2002, 26, 1827-1830
35. Espinas, J.; Darbost, U.; Pelletier, J.; Jeanneau, E.; Duchamp, C.; Bayard, F.; Boyron, O.; Broyer, J. P.; Thivolle-Cazat, J.; Basset, J. M.; Taoufik, M.; Bonnamour, I. Eur. J. Inorg. Chem. 2010, 1349-1359
36. Jaime, C.; De Mendoza, J.; Prados, P.; Nieto, P. M.; Sanchez, C. J. Org. Chem. 1991, 56, 3372-3376
37. Gutsche, C. D.; Reddy, P. A. J. Org. Chem. 1991, 56, 4783-4791
38. Stoikov, I. I.; Khrustalev, A. A.; Antipin, I. S.; Konovalov, A. I. Dokl. Akad. Nauk 2000, 374, 202-205