The first heterotriquinone and dicyano-heterotriquinone methide that undergo a five-stage amphoteric redox reaction

Angewandte Chemie - International Edition

Volumn 37, Issue 18, 1998, Pages 2484-2487

  Takahashi, Kazuko ^a   Fujita, Satoshi ^a   Akiyama, Kimio ^a   Miki, Misao ^b   Yanagi, Kazunori ^b  

^a TOHOKU UNIVERSITY   (Japan)

^b SUMITOMO CHEMICAL CO LTD   (Japan)

Author keywords

Heterocycles; Quinones; Radical ions; Redox chemistry

Indexed keywords

EID: 0032476169     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981002)37:18<2484::AID-ANIE2484>3.0.CO;2-B     Document Type: Article

References (29)

1. For some recent examples see: K. Takahashi, Pure Appl. Chem. 1993, 65, 127; G. M. Tsivgoulis, J.-M. Lehn, Angew. Chem. 1995, 107, 1188; Angew. Chem. Int. Ed. Engl. 1995, 34, 1119; M. Munakata, L. P. Wu, T. K.-Sowa, M. Maekawa, Y. Suenaga, K. Furuichi, J. Am. Chem. Soc. 1996, 118, 3305; M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc. Chem. Commun. 1992, 206; T. Saika, T. Iyoda, K. Honda, T. Shimidzu, J. Chem. Soc. Chem. Commun. 1992, 591; S. Tarutani, T. Mori, H. Mori, S. Tanaka, K. Takahashi, Chem. Lett. 1997, 627.
2. For some recent examples see: K. Takahashi, Pure Appl. Chem. 1993, 65, 127; G. M. Tsivgoulis, J.-M. Lehn, Angew. Chem. 1995, 107, 1188; Angew. Chem. Int. Ed. Engl. 1995, 34, 1119; M. Munakata, L. P. Wu, T. K.-Sowa, M. Maekawa, Y. Suenaga, K. Furuichi, J. Am. Chem. Soc. 1996, 118, 3305; M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc. Chem. Commun. 1992, 206; T. Saika, T. Iyoda, K. Honda, T. Shimidzu, J. Chem. Soc. Chem. Commun. 1992, 591; S. Tarutani, T. Mori, H. Mori, S. Tanaka, K. Takahashi, Chem. Lett. 1997, 627.
3. For some recent examples see: K. Takahashi, Pure Appl. Chem. 1993, 65, 127; G. M. Tsivgoulis, J.-M. Lehn, Angew. Chem. 1995, 107, 1188; Angew. Chem. Int. Ed. Engl. 1995, 34, 1119; M. Munakata, L. P. Wu, T. K.-Sowa, M. Maekawa, Y. Suenaga, K. Furuichi, J. Am. Chem. Soc. 1996, 118, 3305; M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc. Chem. Commun. 1992, 206; T. Saika, T. Iyoda, K. Honda, T. Shimidzu, J. Chem. Soc. Chem. Commun. 1992, 591; S. Tarutani, T. Mori, H. Mori, S. Tanaka, K. Takahashi, Chem. Lett. 1997, 627.
4. For some recent examples see: K. Takahashi, Pure Appl. Chem. 1993, 65, 127; G. M. Tsivgoulis, J.-M. Lehn, Angew. Chem. 1995, 107, 1188; Angew. Chem. Int. Ed. Engl. 1995, 34, 1119; M. Munakata, L. P. Wu, T. K.-Sowa, M. Maekawa, Y. Suenaga, K. Furuichi, J. Am. Chem. Soc. 1996, 118, 3305; M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc. Chem. Commun. 1992, 206; T. Saika, T. Iyoda, K. Honda, T. Shimidzu, J. Chem. Soc. Chem. Commun. 1992, 591; S. Tarutani, T. Mori, H. Mori, S. Tanaka, K. Takahashi, Chem. Lett. 1997, 627.
5. For some recent examples see: K. Takahashi, Pure Appl. Chem. 1993, 65, 127; G. M. Tsivgoulis, J.-M. Lehn, Angew. Chem. 1995, 107, 1188; Angew. Chem. Int. Ed. Engl. 1995, 34, 1119; M. Munakata, L. P. Wu, T. K.-Sowa, M. Maekawa, Y. Suenaga, K. Furuichi, J. Am. Chem. Soc. 1996, 118, 3305; M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc. Chem. Commun. 1992, 206; T. Saika, T. Iyoda, K. Honda, T. Shimidzu, J. Chem. Soc. Chem. Commun. 1992, 591; S. Tarutani, T. Mori, H. Mori, S. Tanaka, K. Takahashi, Chem. Lett. 1997, 627.
6. For some recent examples see: K. Takahashi, Pure Appl. Chem. 1993, 65, 127; G. M. Tsivgoulis, J.-M. Lehn, Angew. Chem. 1995, 107, 1188; Angew. Chem. Int. Ed. Engl. 1995, 34, 1119; M. Munakata, L. P. Wu, T. K.-Sowa, M. Maekawa, Y. Suenaga, K. Furuichi, J. Am. Chem. Soc. 1996, 118, 3305; M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc. Chem. Commun. 1992, 206; T. Saika, T. Iyoda, K. Honda, T. Shimidzu, J. Chem. Soc. Chem. Commun. 1992, 591; S. Tarutani, T. Mori, H. Mori, S. Tanaka, K. Takahashi, Chem. Lett. 1997, 627.
7. For some recent examples see: K. Takahashi, Pure Appl. Chem. 1993, 65, 127; G. M. Tsivgoulis, J.-M. Lehn, Angew. Chem. 1995, 107, 1188; Angew. Chem. Int. Ed. Engl. 1995, 34, 1119; M. Munakata, L. P. Wu, T. K.-Sowa, M. Maekawa, Y. Suenaga, K. Furuichi, J. Am. Chem. Soc. 1996, 118, 3305; M. Hanazawa, R. Sumiya, Y. Horikawa, M. Irie, J. Chem. Soc. Chem. Commun. 1992, 206; T. Saika, T. Iyoda, K. Honda, T. Shimidzu, J. Chem. Soc. Chem. Commun. 1992, 591; S. Tarutani, T. Mori, H. Mori, S. Tanaka, K. Takahashi, Chem. Lett. 1997, 627.
8. a) K. Takahashi, A. Gunji, K. Yanagi, M. Miki, J. Org. Chem. 1996, 61, 4784;
9. b) K. Takahashi, T. Suzuki, J. Am. Chem. Soc. 1989, 111, 5483.
10. For some recent examples: T. Benincori, E. Brenna, F. Sannicolo, L. Trimarco, G. Zotti, P. Sozzani, Angew. Chem. 1996, 108, 718; Angew. Chem. Int. Ed. Engl. 1996, 35, 648; F. Würthner, M. S. Vollmer, F. Effenberger, P. Emele, D. U. Meyer, H. Port, H. C. Wolf, J. Am. Chem. Soc. 1995, 117, 8090; J. Daub, J. Salbeck, T. Knöchel, C. Fisher, H. Kunkey, K. M. Rapp, Angew. Chem. 1989, 101, 1541; Angew. Chem. Int. Ed. Engl. 1989, 28, 1494; A. Knorr, J. Daub, Angew. Chem. 1995, 107, 2925; Angew. Chem. Int. Ed. Engl. 1995, 34, 2664.
11. For some recent examples: T. Benincori, E. Brenna, F. Sannicolo, L. Trimarco, G. Zotti, P. Sozzani, Angew. Chem. 1996, 108, 718; Angew. Chem. Int. Ed. Engl. 1996, 35, 648; F. Würthner, M. S. Vollmer, F. Effenberger, P. Emele, D. U. Meyer, H. Port, H. C. Wolf, J. Am. Chem. Soc. 1995, 117, 8090; J. Daub, J. Salbeck, T. Knöchel, C. Fisher, H. Kunkey, K. M. Rapp, Angew. Chem. 1989, 101, 1541; Angew. Chem. Int. Ed. Engl. 1989, 28, 1494; A. Knorr, J. Daub, Angew. Chem. 1995, 107, 2925; Angew. Chem. Int. Ed. Engl. 1995, 34, 2664.
12. For some recent examples: T. Benincori, E. Brenna, F. Sannicolo, L. Trimarco, G. Zotti, P. Sozzani, Angew. Chem. 1996, 108, 718; Angew. Chem. Int. Ed. Engl. 1996, 35, 648; F. Würthner, M. S. Vollmer, F. Effenberger, P. Emele, D. U. Meyer, H. Port, H. C. Wolf, J. Am. Chem. Soc. 1995, 117, 8090; J. Daub, J. Salbeck, T. Knöchel, C. Fisher, H. Kunkey, K. M. Rapp, Angew. Chem. 1989, 101, 1541; Angew. Chem. Int. Ed. Engl. 1989, 28, 1494; A. Knorr, J. Daub, Angew. Chem. 1995, 107, 2925; Angew. Chem. Int. Ed. Engl. 1995, 34, 2664.
13. For some recent examples: T. Benincori, E. Brenna, F. Sannicolo, L. Trimarco, G. Zotti, P. Sozzani, Angew. Chem. 1996, 108, 718; Angew. Chem. Int. Ed. Engl. 1996, 35, 648; F. Würthner, M. S. Vollmer, F. Effenberger, P. Emele, D. U. Meyer, H. Port, H. C. Wolf, J. Am. Chem. Soc. 1995, 117, 8090; J. Daub, J. Salbeck, T. Knöchel, C. Fisher, H. Kunkey, K. M. Rapp, Angew. Chem. 1989, 101, 1541; Angew. Chem. Int. Ed. Engl. 1989, 28, 1494; A. Knorr, J. Daub, Angew. Chem. 1995, 107, 2925; Angew. Chem. Int. Ed. Engl. 1995, 34, 2664.
14. For some recent examples: T. Benincori, E. Brenna, F. Sannicolo, L. Trimarco, G. Zotti, P. Sozzani, Angew. Chem. 1996, 108, 718; Angew. Chem. Int. Ed. Engl. 1996, 35, 648; F. Würthner, M. S. Vollmer, F. Effenberger, P. Emele, D. U. Meyer, H. Port, H. C. Wolf, J. Am. Chem. Soc. 1995, 117, 8090; J. Daub, J. Salbeck, T. Knöchel, C. Fisher, H. Kunkey, K. M. Rapp, Angew. Chem. 1989, 101, 1541; Angew. Chem. Int. Ed. Engl. 1989, 28, 1494; A. Knorr, J. Daub, Angew. Chem. 1995, 107, 2925; Angew. Chem. Int. Ed. Engl. 1995, 34, 2664.
15. For some recent examples: T. Benincori, E. Brenna, F. Sannicolo, L. Trimarco, G. Zotti, P. Sozzani, Angew. Chem. 1996, 108, 718; Angew. Chem. Int. Ed. Engl. 1996, 35, 648; F. Würthner, M. S. Vollmer, F. Effenberger, P. Emele, D. U. Meyer, H. Port, H. C. Wolf, J. Am. Chem. Soc. 1995, 117, 8090; J. Daub, J. Salbeck, T. Knöchel, C. Fisher, H. Kunkey, K. M. Rapp, Angew. Chem. 1989, 101, 1541; Angew. Chem. Int. Ed. Engl. 1989, 28, 1494; A. Knorr, J. Daub, Angew. Chem. 1995, 107, 2925; Angew. Chem. Int. Ed. Engl. 1995, 34, 2664.
16. For some recent examples: T. Benincori, E. Brenna, F. Sannicolo, L. Trimarco, G. Zotti, P. Sozzani, Angew. Chem. 1996, 108, 718; Angew. Chem. Int. Ed. Engl. 1996, 35, 648; F. Würthner, M. S. Vollmer, F. Effenberger, P. Emele, D. U. Meyer, H. Port, H. C. Wolf, J. Am. Chem. Soc. 1995, 117, 8090; J. Daub, J. Salbeck, T. Knöchel, C. Fisher, H. Kunkey, K. M. Rapp, Angew. Chem. 1989, 101, 1541; Angew. Chem. Int. Ed. Engl. 1989, 28, 1494; A. Knorr, J. Daub, Angew. Chem. 1995, 107, 2925; Angew. Chem. Int. Ed. Engl. 1995, 34, 2664.
17. P. Jordens, G. Rawson, H. Wynberg, J. Chem. Soc. (C), 1970, 273.
18. K. Takahashi, T. Suzuki, K. Akiyama, Y. Ikegami, Y. Fukazawa, J. Am. Chem. Soc. 1991, 113, 4576.
19. +].
20. Kα radiation (λ = 1.54178 Å); T = 296 K. Of a total of 7029 collected reflections, 6558 were unique, and 3227 with I > 3σ (I) were observed. The structure was solved by Patterson methods by using DIRDIF92. Final R factor = 0.054 and Rw factor = 0.073. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-101013. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
21. J. J. Stewart, J. Compt. Chem. 1989, 10, 211.
22. J. B. Torrance, Acc. Chem. Res. 1979, 12, 79.
23. .3- are scarcely different from one another. This can be mainly ascribed to the lack of spin density on the sulfur atoms of these species.
24. 1 value thus is indicative of a compound with a high amphotericity: K. Nakasuji, K. Yoshida, I. Murata, J. Am. Chem. Soc. 1982, 104, 1432; reference [2b], and references therein.
25. J. Heinze, Angew. Chem. 1981, 93, 186; Angew. Chem. Int. Ed. Engl. 1981, 20, 202.
26. J. Heinze, Angew. Chem. 1981, 93, 186; Angew. Chem. Int. Ed. Engl. 1981, 20, 202.
27. J. Rieser, G. A.-Elenien, K. Wallenfels, H. Baumgärtel, Tetahedron Lett. 1976, 2363; T. Kubo, K. Yamamoto, K. Nakasuji, T. Takui, I. Murata, Angew. Chem. 1996, 108, 456; Angew. Chem. Int. Ed. Engl. 1996, 35, 439.
28. J. Rieser, G. A.-Elenien, K. Wallenfels, H. Baumgärtel, Tetahedron Lett. 1976, 2363; T. Kubo, K. Yamamoto, K. Nakasuji, T. Takui, I. Murata, Angew. Chem. 1996, 108, 456; Angew. Chem. Int. Ed. Engl. 1996, 35, 439.
29. J. Rieser, G. A.-Elenien, K. Wallenfels, H. Baumgärtel, Tetahedron Lett. 1976, 2363; T. Kubo, K. Yamamoto, K. Nakasuji, T. Takui, I. Murata, Angew. Chem. 1996, 108, 456; Angew. Chem. Int. Ed. Engl. 1996, 35, 439.