Dibenzotetrathiafulvalenes inserted with cycloalkanes and their tricyclic valence isomers: reversible C–C bond making/breaking upon electron transfer

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Takanori Suzuki, Masahide Kondo, Tatsuo Nakamura, Takanori Fukushima and Tsutomu Miyashi


Abstract

The title TTF derivatives and their tricyclic valence isomers afford the same bicyclic dications upon two-electron oxidation, and the resulting dications regenerate either one or the other of the two isomers selectively upon reduction.


References

  1. P. R. Ashton, R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, S. Menzer, L. Pérez-García, L. Prodi, J. F. Stoddart, M. Venturi, A. J. P. White and D. J. Williams, J. Am. Chem. Soc., 1995, 117, 11 171 CrossRef; D. J. Cárdenas, A. Livoreil and J.-P. Sauvage, J. Am. Chem. Soc., 1996, 118, 11 980 CrossRef CAS.
  2. T. Suzuki, J. Nishida and T. Tsuji, Angew. Chem., Int. Ed. Engl., 1997, 36, 1329 CrossRef CAS; T. Suzuki, H. Shiohara, M. Monobe, T. Sakimura, S. Tanaka, Y. Yamashita and T. Miyashi, Angew. Chem., Int. Ed. Engl., 1992, 31, 455 CrossRef.
  3. S. F. Nelsen and C. R. Kessel, J. Am. Chem. Soc., 1977, 99, 2392 CrossRef CAS; S. F. Nelsen, W. C. Hollinsed, C. R. Kessel and J. C. Calabrese, J. Am. Chem. Soc., 1978, 100, 7876 CrossRef CAS; S. F. Nelsen, D. A. Trieber, J. J. Wolff, D. R. Powell and S. Roger-Crowley, J. Am. Chem. Soc., 1997, 119, 6873 CrossRef CAS.
  4. R. W. Alder, R. Gill and N. C. Goode, J. Chem. Soc., Chem. Commun., 1976, 973 RSC; R. W. Alder and R. B. Sessions, J. Am. Chem. Soc., 1979, 101, 3651 CrossRef CAS; R. W. Alder, A. G. Orpen and J. M. White, J. Chem. Soc., Chem. Commun., 1985, 949 RSC; R. W. Alder, Tetrahedron, 1990, 46, 683 CrossRef CAS.
  5. K.-D. Asmus, Acc. Chem. Res., 1979, 12, 436 CrossRef CAS; W. K. Musker, Acc. Chem. Res., 1980, 13, 200 CrossRef CAS; H. Fujihara, J.-J. Chiu and N. Furukawa, J. Am. Chem. Soc., 1988, 110, 1280 CrossRef CAS.
  6. M. Horner and S. Hünig, J. Am. Chem. Soc., 1977, 99, 6122 CrossRef CAS; W. Freund and S. Hünig, J. Org. Chem., 1987, 52, 2154 CrossRef CAS.
  7. K. Akiba, K. Ishikawa and N. Inamoto, Bull. Chem. Soc. Jpn., 1978, 51, 2674 CAS.
  8. R. Bishop, Aust. J. Chem., 1984, 37, 319 CAS.
  9. A. Gleiter and W. Schäfer, Acc. Chem. Res., 1990, 23, 369 CrossRef CAS.
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