Synthesis of a criss-cross overlapped tetrathiafulvalenophane and a topologically new [2]catenane

Abstract

Using stepwise cyclization reactions followed by an intramolecular coupling, the criss-cross overlapped tetrathiafulvalenophane 8 was readily prepared. The structure of the cis,cis isomer was elucidated by X-ray crystallography which revealed a host–guest complex with chloroform. This electron donor was used for the synthesis of a topologically new type of [2]catenane 11-4PF₆, under ultra-high pressure (10 kbar).

References

1. For a comprehensive review on catenanes, see D. B. Amabilino and J. F. Stoddart, Chem. Rev., 1995, 95, 1154.
2. (a) Z.-T. Li, P. C. Stein, J. Becher, D. Jensen, P. Mørk and N. Svenstrup, Chem. Eur. J., 1996, 6, 624; (b) Z.-T. Li and J. Becher, Chem. Commun., 1996, 639.
3. M. B. Nielsen, Z.-T. Li and J. Becher, J. Mater. Chem., 1997, 7, 1175.
4. P. L. Anelli, P. R. Ashton, R. Ballardini, V. Balzani, M. Delgado, M. T. Gandolfi, T. T. Goodnow, A. E. Kaifer, D. Philp, M. Pietraszkiewicz, L. Prodi, M. V. Reddington, A. M. Z. Slawin, N. Spencer, J. F. Stoddart, C. Vicent and D. J. Williams, J. Am. Chem. Soc., 1992, 114, 193.
5. (a) N. Svenstrup, K. M. Rasmussen, T. K. Hansen and J. Becher, Synthesis, 1994, 809; (b) K. B. Simonsen, N. Svenstrup, J. Lau, O. Simonsen, P. Mørk, G. J. Kristensen and J. Becher, Synthesis, 1996, 3, 407; (c) J. Becher, Z.-T. Li, P. Blanchard, N. Svenstrup, J. Lau, M. B. Nielsen and P. Leriche, Pure Appl. Chem., 1997, 69, 465.
6. For a review on two- three-dimensional tetrathiafulvalenophanes, see M. B. Nielsen and J. Becher, Liebigs Ann., 1997, 2177.
7. (a) K. Takimiya, Y. Shibata, K. Imamura, A. Kashihara, Y. Aso, T. Otsubo and F. Ogura, Tetrahedron Lett., 1995, 28, 5045; (b) J. Tanabe, T. Kudo, M. Okamoto, Y. Kawada, G. Ono, A. Izuoka and T. Sugawara, Chem. Lett., 1995, 579; (c) T. Otsubo, Y. Aso and K. Takimiya, Adv. Mater., 1996, 8, 203; (d) K. Takimiya, K. Imamura, Y. Shibata, Y. Aso, F. Ogura and T. Otsubo, J. Org. Chem., 1997, 62, 5567.
8. (a) F. Vögtle, H. Puff, E. Friedrichs and W. M. Müller, J. Chem. Soc., Chem. Commun., 1982, 1398; (b) I. Tabushi, K. Yamamura, H. Nonoguchi, K. Hirotsu and T. Higuchi, J. Am. Chem. Soc., 1984, 106, 2621; (c) K. Hirotsu, S. Kamitori, T. Higuchi, I. Tabushi, K. Yamamura and H. Nonoguchi, J. Inclusion Phenom., 1984, 2, 215; (d) J. Canceill, L. Lacombe and A. Collet, J. Am. Chem. Soc., 1985, 107, 6993; (e) J. Canceill, M. Cesario, A. Collet, J. Guilhem and C. Pascard, J. Chem. Soc., Chem. Commun., 1985, 361; (f) J. Canceill, M. Cesario, A. Collet, J. Guilhem, C. Riche and C. Pascard, J. Chem. Soc., Chem. Commun., 1986, 339; (g) J. Canceill, L. Lacombe and A. Collet, J. Am. Chem. Soc., 1986, 108, 4230; (h) A. Collet, Tetrahedron, 1987, 43, 5725; (i) J. Canceill, L. Lacombe and A. Collet, J. Chem. Soc., Chem. Commun., 1987, 219; (j) J. Canceill, M. Cesario, A. Collet, J. Guilhem, L. Lacombe, B. Lozach and C. Pascard, Angew. Chem., 1989, 101, 1249; (k) L. F. Lindoy, Nature, 1992, 359, 778; (l) F. Vögtle, J. Gross, C. Seel and M. Nieger, Angew. Chem., Int. Ed. Engl., 1992, 31, 1069.
9. (a) G. M. Sheldrick, SHELXTL Users Manual, Version 5.0, 1994, Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA; (b) G. M. Sheldrick, SHELX-97, 1997, University of Göttingen, Germany.