Quadruple Decker [3.3][3.3][3.3]orthocyclophane acetal - An orthocyclophane ladder

Angewandte Chemie - International Edition

Volumn 37, Issue 18, 1998, Pages 2532-2534

  Mataka, Shuntaro ^a   Shigaki, Kouichiro ^a   Sawada, Tsuyoshi ^a   Mitoma, Yoshihara ^a   Taniguchi, Masahiko ^a   Thiemann, Thies ^a   Ohga, Kazuya ^b   Egashira, Naoyoshi ^b  

^a KYUSHU UNIVERSITY   (Japan)

^b OITA UNIVERSITY   (Japan)

Author keywords

Cations; Cyclic voltammetry; Cyclophanes; Stacking interactions

Indexed keywords

EID: 0032476092     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19981002)37:18<2532::AID-ANIE2532>3.0.CO;2-R     Document Type: Article

References (30)

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2. T. Benzing, T. Tjivikua, J. Wolfe, J. Rebek, Science 1988, 242, 266; S. K. Burley, G. A. Petsko, Science 1985, 229, 23; S. Mataka, J. Ma, T. Thiemann, J. M. Rudziñski, H. Tsuzuki, T. Sawada, M. Tashiro, Tetrahedron 1997, 53, 885-902; D. A. Evans, K. T. Chapman, D. Tan Hung, A. T. Kawaguchi, Angew. Chem. 1987, 99, 1197-1199; Angew. Chem. Int. Ed. Engl. 1987, 26, 1184-1186, and references therein.
3. T. Benzing, T. Tjivikua, J. Wolfe, J. Rebek, Science 1988, 242, 266; S. K. Burley, G. A. Petsko, Science 1985, 229, 23; S. Mataka, J. Ma, T. Thiemann, J. M. Rudziñski, H. Tsuzuki, T. Sawada, M. Tashiro, Tetrahedron 1997, 53, 885-902; D. A. Evans, K. T. Chapman, D. Tan Hung, A. T. Kawaguchi, Angew. Chem. 1987, 99, 1197-1199; Angew. Chem. Int. Ed. Engl. 1987, 26, 1184-1186, and references therein.
4. T. Benzing, T. Tjivikua, J. Wolfe, J. Rebek, Science 1988, 242, 266; S. K. Burley, G. A. Petsko, Science 1985, 229, 23; S. Mataka, J. Ma, T. Thiemann, J. M. Rudziñski, H. Tsuzuki, T. Sawada, M. Tashiro, Tetrahedron 1997, 53, 885-902; D. A. Evans, K. T. Chapman, D. Tan Hung, A. T. Kawaguchi, Angew. Chem. 1987, 99, 1197-1199; Angew. Chem. Int. Ed. Engl. 1987, 26, 1184-1186, and references therein.
5. T. Benzing, T. Tjivikua, J. Wolfe, J. Rebek, Science 1988, 242, 266; S. K. Burley, G. A. Petsko, Science 1985, 229, 23; S. Mataka, J. Ma, T. Thiemann, J. M. Rudziñski, H. Tsuzuki, T. Sawada, M. Tashiro, Tetrahedron 1997, 53, 885-902; D. A. Evans, K. T. Chapman, D. Tan Hung, A. T. Kawaguchi, Angew. Chem. 1987, 99, 1197-1199; Angew. Chem. Int. Ed. Engl. 1987, 26, 1184-1186, and references therein.
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10. See D. J. Cram, R. H. Bauer, J. Am. Chem. Soc. 1959, 81, 5971-5977; L. A. Singer, D. J. Cram, J. Am. Chem. Soc. 1963, 85, 1080-1084.
11. Review: S. M. Rosenfeld, K. A. Choe in Cyclophanes (Eds.: P. M. Keehn, S. M. Rosenfeld), Academic Press, New York, 1983.
12. Paracyclophanes show a bathochromic shift in their UV/Vis spectra relative to similarly substituted open-chain arenes. This effect is partly the result of the deformation of the aromatic system. D. Cram has shown that by shortening the ansachain of [n]paracyclophanes a bathochromic shift can be observed as a consequence of the deformation of the aromatic ring: D. J. Cram, C. S. Montgomery. G. R. Knox, J. Am. Chem. Soc. 1966, 88, 515-525.
13. Nevertheless, the absorption spectra in multilayered [2.2]paracyclophanes show both a bathochromic and a hyperchromic shift with an increasing number of layers. This effect can be quite large relative to that seen in double-layered [2.2]paracyclophanes, and can only result from transannular π-π electronic interactions: T. Otsubo, S. Mizogami, J. Otsubo, Z. Tozuka, A. Sakagami, Y. Sakata, S. Misumi, Bull. Chem. Soc. Jpn. 1973, 46, 3519-3530; S. Misumi, Multilayered Cyclophanes in reference [5].
14. Nevertheless, the absorption spectra in multilayered [2.2]paracyclophanes show both a bathochromic and a hyperchromic shift with an increasing number of layers. This effect can be quite large relative to that seen in double-layered [2.2]paracyclophanes, and can only result from transannular π-π electronic interactions: T. Otsubo, S. Mizogami, J. Otsubo, Z. Tozuka, A. Sakagami, Y. Sakata, S. Misumi, Bull. Chem. Soc. Jpn. 1973, 46, 3519-3530; S. Misumi, Multilayered Cyclophanes in reference [5].
15. See also: F. Vögtle, Cyclophane Chemistry - Synthesis, Structures and Reactions, Wiley, Chichester, 1993, pp. 57-58.
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21. d) S. Mataka, K. Takahashi, T. Hirota, K. Takuma, H. Kobayashi, M. Tashiro, J. Chem. Soc. Chem. Commun. 1985, 973-973.
22. a) S. Mataka, K. Takahashi, T. Mimura, T. Hirota, K. Takuma, H. Kobayashi, M. Yashiro, K. Imada, M. Kuniyoshi, J. Org. Chem. 1987, 52, 2653-2656;
23. b) S. Mataka, Y. Mitoma, T. Sawada, M. Tashiro, Tetrahedron Lett. 1996, 37, 65-68;
24. c) S. Mataka, Y. Mitoma, T. Thiemann, T. Sawada, M. Taniguchi, M. Kobuchi, M. Tashiro, Tetrahedron 1997, 53, 3015-3026.
25. 3) both lead to rigid layered [3.3]orthocyclophanes. (Equation Presented)
26. S. Mataka, M. Taniguchi, Y. Mitoma, T. Sawada, M. Tashiro, J. Chem. Res. Synop. 1997 48-49; J. Chem. Res. Miniprint 1997, 437-452.
27. S. Mataka, M. Taniguchi, Y. Mitoma, T. Sawada, M. Tashiro, J. Chem. Res. Synop. 1997 48-49; J. Chem. Res. Miniprint 1997, 437-452.
28. Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101215. 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).
29. 3CN)] = +0.53 V versus normal hydrogen electrode (NHE); see also: C. K. Mann, "Nonaqueous Solvents for Electrochemical Use" in Electroanalytical Chemistry, Vol. 3, (Ed.: A. J. Bard), Marcel Dekker, New York, 1969, p. 64.
30. M. Dietrich, J. Mortensen, J. Heinze, J. Chem. Soc. Chem. Commun. 1986, 1131-1132, and references therein.