Preparation, structure, and redox reactions of nine-membered cyclic peroxides: A novel electrochromic system undergoing reversible extrusion and trapping of O2

Angewandte Chemie - International Edition

Volumn 39, Issue 10, 2000, Pages 1804-1806

  Suzuki, Takanori ^a   Nishida, Jun ichi ^a   Ohkita, Masakazu ^a   Tsuji, Takashi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Electrochemistry; Oxygen; Peroxides; Redox chemistry

Indexed keywords

OXYGEN; PEROXIDE;

ARTICLE; CHEMICAL STRUCTURE; ELECTRON TRANSPORT; GEOMETRY; ORGANIC CHEMISTRY; OXIDATION REDUCTION REACTION; STRUCTURE ANALYSIS; X RAY ANALYSIS;

EID: 0034657465     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(20000515)39:10<1804::AID-ANIE1804>3.0.CO;2-3     Document Type: Article

References (26)

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2. A. Robert, B. Meunier, Chem. Soc. Rev. 1998, 27, 273; C. W. Jefford, S. Kohmoto, D. Jaggi, G. Timári, J.-C. Rossier, M. Rudaz, O. Barbuzzi, D. Gérard, U. Burger, P. Kamalaprija, J. Mareda, G. Bernardinelli, I. Manzanares, C. J. Canfield, S. L. Fleck, B. L. Robinson, W. Peters, Helv. Chim. Acta 1995, 78, 647; G. H. Posner, J. N. Cumming, P. Ploypradith, C. H. Oh, J. Am. Chem. Soc. 1995, 117, 5885.
3. A. Robert, B. Meunier, Chem. Soc. Rev. 1998, 27, 273; C. W. Jefford, S. Kohmoto, D. Jaggi, G. Timári, J.-C. Rossier, M. Rudaz, O. Barbuzzi, D. Gérard, U. Burger, P. Kamalaprija, J. Mareda, G. Bernardinelli, I. Manzanares, C. J. Canfield, S. L. Fleck, B. L. Robinson, W. Peters, Helv. Chim. Acta 1995, 78, 647; G. H. Posner, J. N. Cumming, P. Ploypradith, C. H. Oh, J. Am. Chem. Soc. 1995, 117, 5885.
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6. Y. Takahashi, K. Wakamatsu, S. Morishima, T. Miyashi, J. Chem. Soc. Perkin Trans. 2 1993, 243; Y. Takahashi, S. Morishima, K. Wakamatsu, T. Suzuki, T. Miyashi, J. Chem. Soc. Chem. Commun. 1994, 13.
7. Y. Takahashi, K. Wakamatsu, S. Morishima, T. Miyashi, J. Chem. Soc. Perkin Trans. 2 1993, 243; Y. Takahashi, S. Morishima, K. Wakamatsu, T. Suzuki, T. Miyashi, J. Chem. Soc. Chem. Commun. 1994, 13.
8. Y. Ushigoe, Y. Torao, A. Masuyama, M. Nojima, J. Org. Chem. 1997, 62, 4949; Y. Takahashi, M. Ando, T. Miyashi, Tetrahderon Lett. 1995, 36, 1889; W. Fenical, J. Am. Chem. Soc. 1974, 96, 5580.
9. Y. Ushigoe, Y. Torao, A. Masuyama, M. Nojima, J. Org. Chem. 1997, 62, 4949; Y. Takahashi, M. Ando, T. Miyashi, Tetrahderon Lett. 1995, 36, 1889; W. Fenical, J. Am. Chem. Soc. 1974, 96, 5580.
10. Y. Ushigoe, Y. Torao, A. Masuyama, M. Nojima, J. Org. Chem. 1997, 62, 4949; Y. Takahashi, M. Ando, T. Miyashi, Tetrahderon Lett. 1995, 36, 1889; W. Fenical, J. Am. Chem. Soc. 1974, 96, 5580.
11. T. Suzuki, J. Nishida, T. Tsuji, Angew. Chem. 1997, 109, 1387; Angew. Chem. Int. Ed. Engl. 1997, 36, 1329.
12. T. Suzuki, J. Nishida, T. Tsuji, Angew. Chem. 1997, 109, 1387; Angew. Chem. Int. Ed. Engl. 1997, 36, 1329.
13. 3CN, 20 C): δ = 8.48 (ddd, J = 6.8, 6.8, 1.5 Hz, 4H), 8.31 (brd, J = 8.3 Hz, 4H), 7.75 (ddd, J = 6.8, 6.8, 1.5 Hz, 2H), 7.73 (dd, J = 8.3, 1.5 Hz, 4H). 7.58 (ddd, J = 6.8, 6.8, 1.0 Hz, 4H), 7.47 (ddd, J = 7.8, 7.8, 1.0 Hz, 2H), 7.37 (dd, J = 7.8, 1.8 Hz, 2H), 7.32 (brd, J = 7.8 Hz, 2H).
14. H. Gilman, W. J. Trepka, J. Org. Chem. 1961, 26, 5202.
15. .., in which the spin density is delocalized over thioxanthyl moieties.
16. 2+ followed by C-O bond making (EEC process).
17. -1, Rw = 0.055. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication nos. CCDC-136844 and -136845. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
18. The O-O bond length in 1,4-diphenyl-2,3-dioxabicyclo[2.2.1]heptane is 1.501(2) Å (D. J. Coughlin, R. S. Brown, R. G. Salomon, J. Am. Chem. Soc. 1979, 101, 1533) and that in tetrahenzopentacene endoperoxide is 1.496(5) Å ( A. Izuoka, T. Murase, M. Tsukada, Y. Ito, T. Sugawara, A. Uchida, N. Sato, H. Inokuchi, Tetrahedron Lett. 1997, 38, 245). Long O-O distances are more common for small ring peroxides, such as dioxiranes (1.503(5) Å for dimesityldioxirane: W. Sander, K. Schroeder, S. Muthusamy, A. Kirschfeld, W. Kappert, R. Boese, E. Kraka, C. Sosa, D. Cremer, J. Am. Chem. Soc. 1997, 119, 7265) or dioxetanes (1.500 and 1.55 Å in 1,6-diphenyl-2,5,7,8-tetraoxobicyclo[4.2.0]octane derivatives: W. Adam, E. Schmidt, E.-M. Peters, K. Peters, H. G. von Schnering, Angew. Chem. 1983, 95, 566; Angew. Chem. Int. Ed. Engl. 1983, 22, 546). The last one is surprisingly long for an O-O bond although the error in the determination was not given.
19. The O-O bond length in 1,4-diphenyl-2,3-dioxabicyclo[2.2.1]heptane is 1.501(2) Å (D. J. Coughlin, R. S. Brown, R. G. Salomon, J. Am. Chem. Soc. 1979, 101, 1533) and that in tetrahenzopentacene endoperoxide is 1.496(5) Å ( A. Izuoka, T. Murase, M. Tsukada, Y. Ito, T. Sugawara, A. Uchida, N. Sato, H. Inokuchi, Tetrahedron Lett. 1997, 38, 245). Long O-O distances are more common for small ring peroxides, such as dioxiranes (1.503(5) Å for dimesityldioxirane: W. Sander, K. Schroeder, S. Muthusamy, A. Kirschfeld, W. Kappert, R. Boese, E. Kraka, C. Sosa, D. Cremer, J. Am. Chem. Soc. 1997, 119, 7265) or dioxetanes (1.500 and 1.55 Å in 1,6-diphenyl-2,5,7,8-tetraoxobicyclo[4.2.0]octane derivatives: W. Adam, E. Schmidt, E.-M. Peters, K. Peters, H. G. von Schnering, Angew. Chem. 1983, 95, 566; Angew. Chem. Int. Ed. Engl. 1983, 22, 546). The last one is surprisingly long for an O-O bond although the error in the determination was not given.
20. The O-O bond length in 1,4-diphenyl-2,3-dioxabicyclo[2.2.1]heptane is 1.501(2) Å (D. J. Coughlin, R. S. Brown, R. G. Salomon, J. Am. Chem. Soc. 1979, 101, 1533) and that in tetrahenzopentacene endoperoxide is 1.496(5) Å ( A. Izuoka, T. Murase, M. Tsukada, Y. Ito, T. Sugawara, A. Uchida, N. Sato, H. Inokuchi, Tetrahedron Lett. 1997, 38, 245). Long O-O distances are more common for small ring peroxides, such as dioxiranes (1.503(5) Å for dimesityldioxirane: W. Sander, K. Schroeder, S. Muthusamy, A. Kirschfeld, W. Kappert, R. Boese, E. Kraka, C. Sosa, D. Cremer, J. Am. Chem. Soc. 1997, 119, 7265) or dioxetanes (1.500 and 1.55 Å in 1,6-diphenyl-2,5,7,8-tetraoxobicyclo[4.2.0]octane derivatives: W. Adam, E. Schmidt, E.-M. Peters, K. Peters, H. G. von Schnering, Angew. Chem. 1983, 95, 566; Angew. Chem. Int. Ed. Engl. 1983, 22, 546). The last one is surprisingly long for an O-O bond although the error in the determination was not given.
21. The O-O bond length in 1,4-diphenyl-2,3-dioxabicyclo[2.2.1]heptane is 1.501(2) Å (D. J. Coughlin, R. S. Brown, R. G. Salomon, J. Am. Chem. Soc. 1979, 101, 1533) and that in tetrahenzopentacene endoperoxide is 1.496(5) Å ( A. Izuoka, T. Murase, M. Tsukada, Y. Ito, T. Sugawara, A. Uchida, N. Sato, H. Inokuchi, Tetrahedron Lett. 1997, 38, 245). Long O-O distances are more common for small ring peroxides, such as dioxiranes (1.503(5) Å for dimesityldioxirane: W. Sander, K. Schroeder, S. Muthusamy, A. Kirschfeld, W. Kappert, R. Boese, E. Kraka, C. Sosa, D. Cremer, J. Am. Chem. Soc. 1997, 119, 7265) or dioxetanes (1.500 and 1.55 Å in 1,6-diphenyl-2,5,7,8-tetraoxobicyclo[4.2.0]octane derivatives: W. Adam, E. Schmidt, E.-M. Peters, K. Peters, H. G. von Schnering, Angew. Chem. 1983, 95, 566; Angew. Chem. Int. Ed. Engl. 1983, 22, 546). The last one is surprisingly long for an O-O bond although the error in the determination was not given.
22. The O-O bond length in 1,4-diphenyl-2,3-dioxabicyclo[2.2.1]heptane is 1.501(2) Å (D. J. Coughlin, R. S. Brown, R. G. Salomon, J. Am. Chem. Soc. 1979, 101, 1533) and that in tetrahenzopentacene endoperoxide is 1.496(5) Å ( A. Izuoka, T. Murase, M. Tsukada, Y. Ito, T. Sugawara, A. Uchida, N. Sato, H. Inokuchi, Tetrahedron Lett. 1997, 38, 245). Long O-O distances are more common for small ring peroxides, such as dioxiranes (1.503(5) Å for dimesityldioxirane: W. Sander, K. Schroeder, S. Muthusamy, A. Kirschfeld, W. Kappert, R. Boese, E. Kraka, C. Sosa, D. Cremer, J. Am. Chem. Soc. 1997, 119, 7265) or dioxetanes (1.500 and 1.55 Å in 1,6-diphenyl-2,5,7,8-tetraoxobicyclo[4.2.0]octane derivatives: W. Adam, E. Schmidt, E.-M. Peters, K. Peters, H. G. von Schnering, Angew. Chem. 1983, 95, 566; Angew. Chem. Int. Ed. Engl. 1983, 22, 546). The last one is surprisingly long for an O-O bond although the error in the determination was not given.
23. 2.
24. P. M. S. Monk, R. J. Mortimer, D. R. Rosseinsky, Electrochromism: Fundamentals and Applications, VCH, Weinheim, 1995, pp. 124-182; S. Hünig, M. Kemmer, H. Wenner, I. F. Perepichka, P. Bäuerle, A. Emge, G. Gescheid, Chem. Eur. J. 1999, 5, 1969.
25. P. M. S. Monk, R. J. Mortimer, D. R. Rosseinsky, Electrochromism: Fundamentals and Applications, VCH, Weinheim, 1995, pp. 124-182; S. Hünig, M. Kemmer, H. Wenner, I. F. Perepichka, P. Bäuerle, A. Emge, G. Gescheid, Chem. Eur. J. 1999, 5, 1969.
26. 2+.