Calixarenes with exo-hydroxy groups: Synthesis, crystal and molecular structure of ortho-tert-butylphenol-based calix[4]-, calix[6]- and calix[8]arenes

Tetrahedron

Volumn 53, Issue 9, 1997, Pages 3287-3300

  Sartori, Giovanni ^a   Porta, Cecilia ^a   Bigi, Franca ^a   Maggi, Raimondo ^a   Peri, Francesco ^a   Marzi, Elena ^a   Lanfranchi, Maurizio ^b   Pellinghelli, Maria Angela ^b  

^a Dipto di Chimica Organica   (Italy)

^b CNR   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE; MACROCYCLIC COMPOUND;

ARTICLE; CHEMICAL STRUCTURE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; X RAY CRYSTALLOGRAPHY;

EID: 0031550814     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00039-2     Document Type: Article

References (35)

1. 1. Gutsche, C.D. "Calixarenes", The Royal Society of Chemistry, Cambridge, England, 1989; "Calixarenes. A versatile Class of Macrocyclic Compounds", Vicens, J. and Böhmer, V. Eds., Kluwer, Dordrecht, 1991; Cram, D.J.; Cram, J.M. "Container Molecules and Their Guests", The Royal Society of Chemistry, Cambridge, England, 1984, pp 85-130; Shinkai, S. Tetrahedron, 1993, 49, 8933; Böhmer, V. Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
2. 1. Gutsche, C.D. "Calixarenes", The Royal Society of Chemistry, Cambridge, England, 1989; "Calixarenes. A versatile Class of Macrocyclic Compounds", Vicens, J. and Böhmer, V. Eds., Kluwer, Dordrecht, 1991; Cram, D.J.; Cram, J.M. "Container Molecules and Their Guests", The Royal Society of Chemistry, Cambridge, England, 1984, pp 85-130; Shinkai, S. Tetrahedron, 1993, 49, 8933; Böhmer, V. Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
3. 1. Gutsche, C.D. "Calixarenes", The Royal Society of Chemistry, Cambridge, England, 1989; "Calixarenes. A versatile Class of Macrocyclic Compounds", Vicens, J. and Böhmer, V. Eds., Kluwer, Dordrecht, 1991; Cram, D.J.; Cram, J.M. "Container Molecules and Their Guests", The Royal Society of Chemistry, Cambridge, England, 1984, pp 85-130; Shinkai, S. Tetrahedron, 1993, 49, 8933; Böhmer, V. Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
4. 1. Gutsche, C.D. "Calixarenes", The Royal Society of Chemistry, Cambridge, England, 1989; "Calixarenes. A versatile Class of Macrocyclic Compounds", Vicens, J. and Böhmer, V. Eds., Kluwer, Dordrecht, 1991; Cram, D.J.; Cram, J.M. "Container Molecules and Their Guests", The Royal Society of Chemistry, Cambridge, England, 1984, pp 85-130; Shinkai, S. Tetrahedron, 1993, 49, 8933; Böhmer, V. Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
5. 1. Gutsche, C.D. "Calixarenes", The Royal Society of Chemistry, Cambridge, England, 1989; "Calixarenes. A versatile Class of Macrocyclic Compounds", Vicens, J. and Böhmer, V. Eds., Kluwer, Dordrecht, 1991; Cram, D.J.; Cram, J.M. "Container Molecules and Their Guests", The Royal Society of Chemistry, Cambridge, England, 1984, pp 85-130; Shinkai, S. Tetrahedron, 1993, 49, 8933; Böhmer, V. Angew. Chem., Int. Ed. Engl., 1995, 34, 713.
6. 2. Gutsche, C.D.; Muthukrishnan, R. J. Org. Chem., 1978, 43, 4905; Muthukrishnan, R.; Gutsche, C.D. ibid., 1979, 44, 3962; Gutsche, C.D.; Dhawan, B.; No, K.H.; Muthukrishnan, R. J. Am. Chem. Soc., 1981, 103, 3782.
7. 2. Gutsche, C.D.; Muthukrishnan, R. J. Org. Chem., 1978, 43, 4905; Muthukrishnan, R.; Gutsche, C.D. ibid., 1979, 44, 3962; Gutsche, C.D.; Dhawan, B.; No, K.H.; Muthukrishnan, R. J. Am. Chem. Soc., 1981, 103, 3782.
8. 2. Gutsche, C.D.; Muthukrishnan, R. J. Org. Chem., 1978, 43, 4905; Muthukrishnan, R.; Gutsche, C.D. ibid., 1979, 44, 3962; Gutsche, C.D.; Dhawan, B.; No, K.H.; Muthukrishnan, R. J. Am. Chem. Soc., 1981, 103, 3782.
9. 3. Högberg, A.G. J. Am. Chem. Soc., 1981, 103, 3782; Högberg, A.G. J. Org. Chem., 1980, 45, 4498.
10. 3. Högberg, A.G. J. Am. Chem. Soc., 1981, 103, 3782; Högberg, A.G. J. Org. Chem., 1980, 45, 4498.
11. 4. Shinkai, S. Adv. Supramol. Chem., 1993, 3, 97; Atwood, J.L.; Orr, G.W.; Robinson, K.D.; Hamada, F. Supramol. Chem., 1993, 2, 309; Arduini, A.; Casnati, A.; Fabbi, M.; Minari, P.; Pochini, A.; Sicuri, A.R.; Ungaro, R. Supramol. Chem., 1993, 1, 235; van Loon J.D.; Verboom, W.; Reinhoudt, D.N. Org. Prep. Proc. Int., 1992, 24, 437; Dowden, J.; Kilburn, J.D.; Wright, P. Contemporary Org. Synth., 1995, 2, 289.
12. 4. Shinkai, S. Adv. Supramol. Chem., 1993, 3, 97; Atwood, J.L.; Orr, G.W.; Robinson, K.D.; Hamada, F. Supramol. Chem., 1993, 2, 309; Arduini, A.; Casnati, A.; Fabbi, M.; Minari, P.; Pochini, A.; Sicuri, A.R.; Ungaro, R. Supramol. Chem., 1993, 1, 235; van Loon J.D.; Verboom, W.; Reinhoudt, D.N. Org. Prep. Proc. Int., 1992, 24, 437; Dowden, J.; Kilburn, J.D.; Wright, P. Contemporary Org. Synth., 1995, 2, 289.
13. 4. Shinkai, S. Adv. Supramol. Chem., 1993, 3, 97; Atwood, J.L.; Orr, G.W.; Robinson, K.D.; Hamada, F. Supramol. Chem., 1993, 2, 309; Arduini, A.; Casnati, A.; Fabbi, M.; Minari, P.; Pochini, A.; Sicuri, A.R.; Ungaro, R. Supramol. Chem., 1993, 1, 235; van Loon J.D.; Verboom, W.; Reinhoudt, D.N. Org. Prep. Proc. Int., 1992, 24, 437; Dowden, J.; Kilburn, J.D.; Wright, P. Contemporary Org. Synth., 1995, 2, 289.
14. 4. Shinkai, S. Adv. Supramol. Chem., 1993, 3, 97; Atwood, J.L.; Orr, G.W.; Robinson, K.D.; Hamada, F. Supramol. Chem., 1993, 2, 309; Arduini, A.; Casnati, A.; Fabbi, M.; Minari, P.; Pochini, A.; Sicuri, A.R.; Ungaro, R. Supramol. Chem., 1993, 1, 235; van Loon J.D.; Verboom, W.; Reinhoudt, D.N. Org. Prep. Proc. Int., 1992, 24, 437; Dowden, J.; Kilburn, J.D.; Wright, P. Contemporary Org. Synth., 1995, 2, 289.
15. 4. Shinkai, S. Adv. Supramol. Chem., 1993, 3, 97; Atwood, J.L.; Orr, G.W.; Robinson, K.D.; Hamada, F. Supramol. Chem., 1993, 2, 309; Arduini, A.; Casnati, A.; Fabbi, M.; Minari, P.; Pochini, A.; Sicuri, A.R.; Ungaro, R. Supramol. Chem., 1993, 1, 235; van Loon J.D.; Verboom, W.; Reinhoudt, D.N. Org. Prep. Proc. Int., 1992, 24, 437; Dowden, J.; Kilburn, J.D.; Wright, P. Contemporary Org. Synth., 1995, 2, 289.
16. 5. Chasar, D.W. J. Org. Chem., 1985, 50, 545.
17. 6. a) Böhmer, V.; Dörrenbächer, R.; Vogt, W.; Zetta, L. Tetrahedron Lett., 1992, 33, 769;
18. b) Thondorf, I.; Brenn, J.; Brandt, W.; Böhmer, V. Tetrahedron Lett., 1995, 36, 6665;
19. c) Böhmer, V.; Dörrenbächer, R.; Frings, M.; Heydenreich, M.; De Paoli, D.; Vogt, W.; Ferguson, G.; Thondorf, I. J. Org. Chem., 1996, 61, 549.
20. 7. Pappalardo, S.; Ferguson, G.; Gallagher, J.F. J. Org. Chem., 1992, 57, 7102.
21. 8. Sartori, G.; Maggi, R.; Bigi, F.; Arienti, A.; Porta, C.; Predieri, G. Tetrahedron, 1994, 50, 10587; Sartori, G.; Bigi, F.; Maggi, R.; Pastorio, A.; Porta, C.; Bonfanti, G. J. Chem. Soc., Perkin Trans 1, 1994, 1879.
22. 8. Sartori, G.; Maggi, R.; Bigi, F.; Arienti, A.; Porta, C.; Predieri, G. Tetrahedron, 1994, 50, 10587; Sartori, G.; Bigi, F.; Maggi, R.; Pastorio, A.; Porta, C.; Bonfanti, G. J. Chem. Soc., Perkin Trans 1, 1994, 1879.
23. 9. Sartori, G.; Maggi, R.; Bigi, F.; Arduini, A.; Pastorio, A.; Porta, C. J. Chem. Soc. Perkin Trans. 1, 1994, 1657; Sartori, G.; Bigi, F.; Porta, C.; Maggi, R.; Peri, F. Tetrahedron Lett., 1995, 36, 8323.
24. 9. Sartori, G.; Maggi, R.; Bigi, F.; Arduini, A.; Pastorio, A.; Porta, C. J. Chem. Soc. Perkin Trans. 1, 1994, 1657; Sartori, G.; Bigi, F.; Porta, C.; Maggi, R.; Peri, F. Tetrahedron Lett., 1995, 36, 8323.
25. 10. Sartori, G.; Bigi, F.; Porta, C.; Maggi, R.; Mora, R. Tetrahedron Lett., 1995, 36, 2311.
26. 11. Casiraghi, G.; Casnati, G.; Pochini, A.; Puglia, G.; Ungaro, R.; Sartori, G. Synthesis, 1981, 143.
27. 12. Tashiro, M.; Fukata, G. Org. Prep. Proc. Int., 1976, 8(5), 231.
28. 13. Konishi, H.; Ohata, K.; Morikawa, O.; Kobayashi, K. J. Chem. Soc., Chem. Comm., 1995, 309.
29. 14. Gutsche, C.D.; Bauer, L.J. J. Am. Chem. Soc., 1985, 107, 6052.
30. 15. Casiraghi, G.; Casnati, G.; Cornia, M.; Pochini, A.; Puglia, G.; Sartori, G.; Ungaro, R. J. Chem. Soc., Perkin Trans. 1, 1978, 318.
31. 16. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Cryst., 1993, 26, 343; "SHELXS-86. Program for the solution of crystal structures", University of Göttingen, Germany 1986; Sheldrick, G. M. "SHELX-76. Program for crystal stucture determination", University of Cambridge, UK 1976; Nardelli, M. Comput. Chem., 1983, 7, 95; Johnson, C.K. "ORTEP. A fortran thermal-ellipsoid plot program for crystal structure illustrations", Rep. ORNL-3794 revised, Oak Ridge National Laboratory, Oak Ridge, TN, USA, 1965.
32. 16. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Cryst., 1993, 26, 343; "SHELXS-86. Program for the solution of crystal structures", University of Göttingen, Germany 1986; Sheldrick, G. M. "SHELX-76. Program for crystal stucture determination", University of Cambridge, UK 1976; Nardelli, M. Comput. Chem., 1983, 7, 95; Johnson, C.K. "ORTEP. A fortran thermal-ellipsoid plot program for crystal structure illustrations", Rep. ORNL-3794 revised, Oak Ridge National Laboratory, Oak Ridge, TN, USA, 1965.
33. 16. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Cryst., 1993, 26, 343; "SHELXS-86. Program for the solution of crystal structures", University of Göttingen, Germany 1986; Sheldrick, G. M. "SHELX-76. Program for crystal stucture determination", University of Cambridge, UK 1976; Nardelli, M. Comput. Chem., 1983, 7, 95; Johnson, C.K. "ORTEP. A fortran thermal-ellipsoid plot program for crystal structure illustrations", Rep. ORNL-3794 revised, Oak Ridge National Laboratory, Oak Ridge, TN, USA, 1965.
34. 16. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Cryst., 1993, 26, 343; "SHELXS-86. Program for the solution of crystal structures", University of Göttingen, Germany 1986; Sheldrick, G. M. "SHELX-76. Program for crystal stucture determination", University of Cambridge, UK 1976; Nardelli, M. Comput. Chem., 1983, 7, 95; Johnson, C.K. "ORTEP. A fortran thermal-ellipsoid plot program for crystal structure illustrations", Rep. ORNL-3794 revised, Oak Ridge National Laboratory, Oak Ridge, TN, USA, 1965.
35. 16. Altomare, A.; Cascarano, G.; Giacovazzo, C.; Guagliardi, A. J. Appl. Cryst., 1993, 26, 343; "SHELXS-86. Program for the solution of crystal structures", University of Göttingen, Germany 1986; Sheldrick, G. M. "SHELX-76. Program for crystal stucture determination", University of Cambridge, UK 1976; Nardelli, M. Comput. Chem., 1983, 7, 95; Johnson, C.K. "ORTEP. A fortran thermal-ellipsoid plot program for crystal structure illustrations", Rep. ORNL-3794 revised, Oak Ridge National Laboratory, Oak Ridge, TN, USA, 1965.