Synthesis, structure, and redox properties of a quinone-bridged calix[6]arene

Tetrahedron Letters

Volumn 41, Issue 6, 2000, Pages 897-901

  Akine, Shigehisa ^a   Goto, Kei ^a   Kawashima, Takayuki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Benzoquinones; Calixarenes; Electrochemistry; X ray crystal structures

Indexed keywords

1,4 BENZOQUINONE; CALIXARENE; QUINONE DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0034606940     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02171-1     Document Type: Article

References (20)

1. For reviews, see: (a) Pochini, A.; Ungaro, R. Comprehensive Supramolecular Chemistry, Vol. 2; Vögtle, P., Ed.; Pergamon: Oxford, 1996; p. 103. (b) Gutsche, C. D. Calixarenes in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1989. (c) Calixarenes: a Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. (d) Gutsche, C. D. Calixarenes Revisited in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998.
2. For reviews, see: (a) Pochini, A.; Ungaro, R. Comprehensive Supramolecular Chemistry, Vol. 2; Vögtle, P., Ed.; Pergamon: Oxford, 1996; p. 103. (b) Gutsche, C. D. Calixarenes in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1989. (c) Calixarenes: a Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. (d) Gutsche, C. D. Calixarenes Revisited in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998.
3. For reviews, see: (a) Pochini, A.; Ungaro, R. Comprehensive Supramolecular Chemistry, Vol. 2; Vögtle, P., Ed.; Pergamon: Oxford, 1996; p. 103. (b) Gutsche, C. D. Calixarenes in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1989. (c) Calixarenes: a Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. (d) Gutsche, C. D. Calixarenes Revisited in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998.
4. For reviews, see: (a) Pochini, A.; Ungaro, R. Comprehensive Supramolecular Chemistry, Vol. 2; Vögtle, P., Ed.; Pergamon: Oxford, 1996; p. 103. (b) Gutsche, C. D. Calixarenes in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1989. (c) Calixarenes: a Versatile Class of Macrocyclic Compounds; Vicens, J.; Böhmer, V., Eds.; Kluwer Academic Publishers: Dordrecht, 1991. (d) Gutsche, C. D. Calixarenes Revisited in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1998.
5. Cram, D. J.; Cram, J. M. Container Molecules and Their Guests in Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; The Royal Society of Chemistry: Cambridge, 1994.
6. (a) Robbins, T. A.; Cram, D. J. J. Am. Chem. Soc. 1993, 115, 12199.
7. (b) Robbins, T. A.; Knobler, C. B.; Bellew, D. R.; Cram, D. J. J. Am. Chem. Soc. 1994, 116, 111.
8. (a) Alvarez, J.; Wang, Y.; Gómez-Kaifer, M.; Kaifer, A. E. Chem. Commun. 1998, 1455.
9. (b) Wang, Y.; Alvarez, J.; Kaifer, A. E. Chem. Commun. 1998, 1457.
10. For examples, see: (a) Morita, Y.; Agawa, T.; Kai, Y.; Kanehisa, N.; Kasai, N.; Nomura, P.; Taniguchi, H. Chem. Lett. 1989, 1349. (b) Suga, K.; Fujihara, M.; Morita, Y.; Agawa, T. J. Chem. Soc., Faraday Trans. 1991, 87, 1575. (c) Morita, Y.; Agawa, T.; Nomura, E.; Taniguchi, H. J. Org. Chem. 1992, 57, 3658. (d) Casnati, A.; Comelli, P.; Fabbi, M.; Bocchi, V.; Mori, G.; Ugozzoli, F.; Lanfredi, A. M. M.; Pochini, A.; Ungaro, R. Recl. Trav. Chim. Pays-Bas 1993, 112, 384.
11. For examples, see: (a) Morita, Y.; Agawa, T.; Kai, Y.; Kanehisa, N.; Kasai, N.; Nomura, P.; Taniguchi, H. Chem. Lett. 1989, 1349. (b) Suga, K.; Fujihara, M.; Morita, Y.; Agawa, T. J. Chem. Soc., Faraday Trans. 1991, 87, 1575. (c) Morita, Y.; Agawa, T.; Nomura, E.; Taniguchi, H. J. Org. Chem. 1992, 57, 3658. (d) Casnati, A.; Comelli, P.; Fabbi, M.; Bocchi, V.; Mori, G.; Ugozzoli, F.; Lanfredi, A. M. M.; Pochini, A.; Ungaro, R. Recl. Trav. Chim. Pays-Bas 1993, 112, 384.
12. For examples, see: (a) Morita, Y.; Agawa, T.; Kai, Y.; Kanehisa, N.; Kasai, N.; Nomura, P.; Taniguchi, H. Chem. Lett. 1989, 1349. (b) Suga, K.; Fujihara, M.; Morita, Y.; Agawa, T. J. Chem. Soc., Faraday Trans. 1991, 87, 1575. (c) Morita, Y.; Agawa, T.; Nomura, E.; Taniguchi, H. J. Org. Chem. 1992, 57, 3658. (d) Casnati, A.; Comelli, P.; Fabbi, M.; Bocchi, V.; Mori, G.; Ugozzoli, F.; Lanfredi, A. M. M.; Pochini, A.; Ungaro, R. Recl. Trav. Chim. Pays-Bas 1993, 112, 384.
13. For examples, see: (a) Morita, Y.; Agawa, T.; Kai, Y.; Kanehisa, N.; Kasai, N.; Nomura, P.; Taniguchi, H. Chem. Lett. 1989, 1349. (b) Suga, K.; Fujihara, M.; Morita, Y.; Agawa, T. J. Chem. Soc., Faraday Trans. 1991, 87, 1575. (c) Morita, Y.; Agawa, T.; Nomura, E.; Taniguchi, H. J. Org. Chem. 1992, 57, 3658. (d) Casnati, A.; Comelli, P.; Fabbi, M.; Bocchi, V.; Mori, G.; Ugozzoli, F.; Lanfredi, A. M. M.; Pochini, A.; Ungaro, R. Recl. Trav. Chim. Pays-Bas 1993, 112, 384.
14. (a) Saiki, T.; Goto, K.; Tokitoh, N.; Okazaki, R. J. Org. Chem. 1996, 61, 2924.
15. (b) Saiki, T.; Goto, K.; Okazaki, R. Chem. Lett. 1996, 993.
16. (c) Saiki, T.; Goto, K.; Okazaki, R. Angew. Chem., Int. Ed. Engl. 1997, 36, 2223.
17. (d) Akine, S.; Goto, K.; Kawashima, T.; Okazaki, R. Bull. Chem. Soc. Jpn. 1999, 72, 2781.
18. (e) Akine, S.; Goto, K.; Kawashima, T. J. Incl. Phenom. Macrocycl. Chem. in press.
19. Chambers, J. Q. The Chemistry of the Quinonoid Compound; Patai, S. Ed.; John Wiley & Sons: London, 1974; Chapter 14.
20. w=0.073 for 1018 parameters.