Syntheses of p-tert-butyloxocalix[4]-, [5]-, and [6]arenes and their behavior in solution

Tetrahedron Letters

Volumn 37, Issue 33, 1996, Pages 5959-5962

  Ito, Kazuaki ^a   Izawa, Soichiro ^a   Ohba, Toshio ^a   Ohba, Yoshihiro ^a   Sone, Tyo ^a  

^a YAMAGATA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CALIXARENE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONFORMATION; HYDROGEN BOND; NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0030581407     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01287-7     Document Type: Article

References (19)

1. 1. a) Gutsche, C.D. Calixarenes, The Royal Society of Chemistry, Cambridge, 1989.
2. b) Böhmer, V. Angew. Chem. Int. Ed. Engl. 1995, 34, 713-745.
3. 2. Sartori, G.; Maggi, R.; Bigi, F.; Arduini, A.; Pastorio, A.; Porta, C. J. Chem. Soc., Perkin 1, 1994, 1657-1658.
4. 3. Glüttner, C.; Böhmer, V.; Vogt, W.; Thondort, I.; Biali, S.E.; Grystzpan, F. Tetrahedron Lett. 1994, 35, 6267-6270.
5. 4. Moshfegh, A.A.; Badri, R.; Hojjatie, M.; Kaviani, M.; Naderi, B.; Nazmi, A.H.; Ramezanian, M.; Roozpenikar, B.; Hakimerahi, G.H. Helv. Chim. Acta 1982, 66, 1221-1228.
6. 5. Ninagawa, A.; Cho, K.; Matsuda, H. Makromol. Chem. 1985, 186, 1397-1385.
7. 6. Görmar, G.; Seiffarth, K.; Schylz, M. Makromol. Chem. 1990, 191, 81-87.
8. 7. The acyclic CO-bridged compounds were prepared analogously to the corresponding tetramer described before; Ohba, Y.; Irie, K.; Zhang, F.S.; Sone, T. Bull. Chem. Soc. Jpn., 1993, 66, 828-835.
9. 7: C,80.28;H,8.37. Found: C,79.98;H,8.24.
10. 9. Gutsche, C.D.; Bauer, L.J. J. Am. Chem. Soc. 1985, 107, 6052-6059.
11. 10. Jaime, C.; de Mendoza, J.; Prado, P.; Nieto, P.M.; Sanchez, C. J. Org. Chem. 1991, 56, 3372-3376.
12. 11. Yamato, T.; Saruwatari, Y.; Nagayama, S.; Maeda, K.; Tashiro, M. J. Chem. Soc., Chem. Commun. 1992, 861-862.
13. 12. Page 89 in ref. 1a.
14. 13. Stewart, D.R.; Krawiec, M.; Kashyap, R.P.; Watson, W.H. Gutsche, C.D. J. Am. Chem. Soc. 1995, 117, 586-601.
15. 1 measurements were made by the inversion recovery method. The deviation of the values is within 5%. The values for the OH groups in 1b and 1c were not determined because of overlapping or broadening of the peaks.
16. 15. Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J.W. Chemistry Lett. 1995, 297-298. Yamada, A.; Murase, T.; Kikukawa, K.; Arimura, T.; Shinkai, S. J. Chem. Soc., Perkin 2, 1991, 793-797. Yamada, A.; Murase, T.; Kikukawa, K.; Matsuda, T.; Shinkai, S. Chemistry Lett. 1990, 455-458. Bauer, L.J.; Gutsche, C.D. J. Am. Chem. Soc. 1985, 107, 6063-6069.
17. 15. Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J.W. Chemistry Lett. 1995, 297-298. Yamada, A.; Murase, T.; Kikukawa, K.; Arimura, T.; Shinkai, S. J. Chem. Soc., Perkin 2, 1991, 793-797. Yamada, A.; Murase, T.; Kikukawa, K.; Matsuda, T.; Shinkai, S. Chemistry Lett. 1990, 455-458. Bauer, L.J.; Gutsche, C.D. J. Am. Chem. Soc. 1985, 107, 6063-6069.
18. 15. Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J.W. Chemistry Lett. 1995, 297-298. Yamada, A.; Murase, T.; Kikukawa, K.; Arimura, T.; Shinkai, S. J. Chem. Soc., Perkin 2, 1991, 793-797. Yamada, A.; Murase, T.; Kikukawa, K.; Matsuda, T.; Shinkai, S. Chemistry Lett. 1990, 455-458. Bauer, L.J.; Gutsche, C.D. J. Am. Chem. Soc. 1985, 107, 6063-6069.
19. 15. Ahn, S.; Chang, S.-K.; Kim, T.; Lee, J.W. Chemistry Lett. 1995, 297-298. Yamada, A.; Murase, T.; Kikukawa, K.; Arimura, T.; Shinkai, S. J. Chem. Soc., Perkin 2, 1991, 793-797. Yamada, A.; Murase, T.; Kikukawa, K.; Matsuda, T.; Shinkai, S. Chemistry Lett. 1990, 455-458. Bauer, L.J.; Gutsche, C.D. J. Am. Chem. Soc. 1985, 107, 6063-6069.