Exploring the chemistry of a double-stranded cycle with the carbon skeleton of the belt region of the C84 fullerene

European Journal of Organic Chemistry

Volumn , Issue 1, 2007, Pages 88-100

  Stuparu, Mihaiela ^a   Lentz, Dieter ^b   Rüegger, Heinz ^a   Schlüter, A Dieter ^a  

^a ETH ZURICH   (Switzerland)

^b FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

Arenes; Aromaticity; Belt shaped compounds; Cyclarenes; Dehydration

Indexed keywords

EID: 33846096323     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600698     Document Type: Article

References (51)

1. a) A. Godt, V. Enkelmann, A. D. Schlüter, Angew. Chem. Int. Ed. Engl. 1989, 28, 1680-1682;
2. b) O. Kintzel, A. D. Schlüter, Acta Polym. 1997, 48, 212-214;
3. c) O. Kintzel, P. Luger, M. Weber, A. D. Schlüter, Eur. J. Org. Chem. 1998, 99-105;
4. d) W. D. Neudorff, D. Lentz, M. Anibarro, A. D. Schlüter, Chem. Eur. J. 2003, 9, 2745-2757.
5. a) P. R. Ashton, G. R. Brown, N. S. Isaacs, D. Giuffrida, F. H. Kohnke, J. P. Mathias, A. M. Z. Slawin, D. R. Smith, J. F. Stoddart, D. J. Williams, J. Am. Chem. Soc. 1992, 114, 6330-6353;
6. b) U. Girreser, D. Giuffrida, F. H. Kohnke, J. P. Mathias, D. Philp, J. F. Stoddart, Pure Appl. Chem. 1993, 65, 119-125;
7. c) A. Schröder, H.-B. Mekelburger, F. Vögtle, Top. Curr. Chem. 1994, 172, 179-201;
8. d) J. Benkhoff, R. Boese, F.-G. Klärner, A. E. Wigger, Tetrahedron Lett. 1994, 35, 73-76;
9. e) R. M. Cory, C. L. McPhail, Tetrahedron Lett. 1996, 37, 1987-1990;
10. f) Y. Kuwatani, T. Yoshida, A. Kusaka, M. Iyoda, Tetrahedron Lett. 2000, 41, 359-363;
11. g) G. J. Bodwell, D. O. Miller, R. J. Vermeij, Org. Lett. 2001, 3, 2093-2096;
12. See also: h) E. Nakamura, K. Tahara, Y. Matsuo, M. Sawamura, J. Am. Chem. Soc. 2003, 125, 2834-2835.
13. For a recent review and book chapter, see: a) L. T. Scott, Angew. Chem. Int. Ed. 2003, 42, 4133-4135;
14. b) R. Gleiter, B. Hellbach, S. Gath, R. J. Schaller, Pure Appl. Chem. 2006, 78, 699-706;
15. c) R. Herges, in: Modern Cyclophane Chemistry, Wiley-VCH, Weinheim, 2004, pp. 337-358.
16. A. D. Schlüter, Adv. Mater. 1991, 3, 282-291;
17. "Synthesis of Polymers": A. D. Schlüter, Material Science and Technology Series, Wiley-VCH, Weinheim 1999, pp. 459-484.
18. S. Kivelson, O. L. Chapman, Phys. Rev. B 1983, 28, 7236-7242.
19. F. H. Kohnke, J. F. Stoddart, Pure Appl. Chem. 1989, 61, 1581-1586.
20. The few representatives beyond heptacene could only be proven in the cationic form: T. Fang, PhD Thesis, UC Los Angeles, 1986.
21. For a theoretical treatment, see: a) M. Kertesz, A. Ashertehrani, Macromolecules 1996, 29, 940-945;
22. b) M. Kertesz, in "Handbook of Organic Conductive Molecules and Polymers" (Ed.: H. S. Nalwa), John Wiley, New York, 1997, vol. 4, p. 147-173.;
23. For polymers and model compounds, which can be prepared and handled because they contain five-membered rings, see: c) A. D. Schlüter, M. Löffler, V. Enkelmann, Nature 1994, 368, 831-834;
24. d) B. Schlicke, H. Schirmer, A. D. Schlüter, Adv. Mater. 1995, 7, 544-546;
25. e) B. Schlicke, A. D. Schlüter, P. Hauser, J. Heinze, Angew. Chem. Int. Ed. Engl. 1997, 36, 1996-1998;
26. f) W. D. Neudorff, N. Schulte, D. Lentz, A. D. Schlüter, Org. Lett. 2001, 3, 3115-3118.
27. [1d].
28. M. Stuparu, A. D. Schlüter, manuscript in preparation.
29. ORTEP3 for Windows: L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
30. The reaction was also performed on a 500 mg scale but yielded the unidentified black material, which distracted us from further experiments on this scale. However, such reactions should, in principle, be possible.
31. The starting material 2 is soluble and was, therefore, previously analyzed by solution NMR spectroscopy.[1d] Its solid-state spectrum was recorded here for a better comparison.
32. H. Bouas-Laurant, J.-P. Desvergne, A. Catellan, R. Lapouyade, Chem. Soc. Rev. 2001, 30, 248-263.
33. For example, see: K. Takegoshi, S. Nakamura, T. Terao, Solid State Nucl. Magn. Reson. 1998, 1, 189-196.
34. For some catalyzed dehydrations, see: a) E. L. Wittbecker, H. K. Hall, Jr., T. W. Campbell, J. Am. Chem. Soc. 1960, 82, 1218-1222;
35. b) L. F. Fieser, M. J. Haddadin, Can. J. Chem. 1965, 43, 1599-1606;
36. c) G. Wittig, W. Reuther, Justus Liebigs Ann. Chem. 1972, 761, 20-24;
37. d) C.-Y. Yick, S.-H. Chan, H. N. C. Wong, Tetrahedron Lett. 2000, 41, 5957-5961;
38. e) T. Hamura, M. Miyamoto, K. Suzuki, Org. Lett. 2002, 4, 229-232;
39. for thermal dehydration, see for example: f) M. A. B. Meador, M. A. Meador, M.-K. Ahn, M. A. Olshavsky, Macromolecules 1989, 22, 4385-4387;
40. for some other relevant references, see: g) W. Nudenberg, L. W. Butz, J. Am. Chem. Soc. 1944, 66, 307-308;
41. h) J. J. Cornejo, S. Ghodsi, R. D. Johnson, R. Woodling, B. Rickborn, J. Org. Chem. 1983, 48, 3869-3876;
42. i) S. Kim, J. H. Park, J. Org. Chem. 1988, 53, 3111-3113;
43. j) X. P. Yang, D. M. Du, Q. Li, T. C. W. Mak, H. N. C. Wong, Chem. Commun. 1999, 16, 1607-1608;
44. k) M. Caldararu, G. Postole, C. Hornoiu, V. Bratan, M. Dragan, N. I. Ionescu, Appl. Surf. Sci. 2001, 181, 255-264;
45. l) A. Pourjavadi, G. B. Marandi, J. Chem. Res. (S) 2002, 11, 552-555;
46. m) J. F. Wen, W. Hong, K. Yuan, T. C. W. Mak, H. N. C. Wong, J. Org. Chem. 2003, 68, 8918-8931;
47. n) G. D. Yadav, A. D. Murkute, Langmuir 2004, 20, 11607-11619.
48. M. Stuparu, A. D. Schlüter, manuscript in preparation.
49. P. E. Eaton, G. R. Carlson, J. T. Lee, J. Org. Chem. 1973, 38, 4071-4073.
50. SAINT: Area-Detector Integration Software, Siemens Industrial Automation, Inc., Madison, WI, 1995.
51. G. M. Sheldrick, SHELX97 - Programs for Crystal Structure Analysis, release 97-2, Institut für Anorganische Chemie der Universität Göttingen, Germany, 1998.