[16.16.16](1,3,5)cyclophanetetracosayne (C60H6): A precursor to C60 fullerene

Journal of the American Chemical Society

Volumn 120, Issue 18, 1998, Pages 4544-4545

  Tobe, Yoshito ^a   Nakagawa, Nobuko ^a   Naemura, Koichiro ^a   Wakabayashi, Tomonari ^b   Shida, Tadamasa ^b   Achiba, Yohji ^c  

^a OSAKA UNIVERSITY   (Japan)

^b KYOTO UNIVERSITY   (Japan)

^c TOKYO METROPOLITAN UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001151203     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja9803308     Document Type: Letter

References (40)

1. For reviews, see: (a) Bethune, D. S.; Johnson, R. D.; Salem, J. R.; de Vries, M. S.; Yannoni, C. S. Nature (London) 1993, 366, 123-128.
2. (b) Edelmann, F. T. Angew. Chem., Int. Ed. Engl. 1995, 34, 981-985.
3. Ph.D. dissertations at UCLA: Jacobsen, R. H. 1986;
4. Xiong, Y. 1987;
5. Loguercio, D., Jr. 1988;
6. Shen, D. 1990.
7. Cited in Diederich, F.; Whetten, R. L. Acc. Chem. Res. 1992, 25, 119-126.
8. Kroto, H. W.; Heath, J. R.; O'Brien, S. C.; Curl, R. F.; Smalley, R. E. Nature (London) 1985, 318, 162-163.
9. Fabre, C.; Rassat, A. C. R. Acad. Sci. Paris 1989, 308, 1223-1228.
10. (b) Rabidau, P. W.; Sygula, A. Acc. Chem. Res. 1996, 29, 235-242.
11. (a) Rubin, Y.; Parker, T. C.; Khan, S. I.; Holliman, C. L.; McElvany, S. W. J. Am. Chem. Soc. 1996, 118, 5308-5309.
12. (b) Rubin, Y. Chem. Eur. J. 1997, 3, 1009-1016.
13. (c) Saalfrank, R. W. Nature (London) 1996, 383, 124-125.
14. (a) von Helden, G.; Gotts, N. G.; Bowers, M. T. Nature (London) 1993, 363, 60-63.
15. (b) Hunter, J. M.; Fye, J. L.; Roskamp, E. J.; Jarrold, M. F. J. Phys. Chem. 1994, 98, 1810-1818.
16. (c) McElvany, S. W.; Ross, M. M.; Goroff, N. S.; Diederich, F. Science 1993, 259, 1594-1596.
17. (d) Strout, D. L.; Scuseria, G. E. J. Phys. Chem. 1996, 100, 6492-6498.
18. (e) For a review, see: Goroff, N. S. Acc. Chem. Res. 1996, 29, 77-83.
19. 60 was undertaken: Ōsawa, E.; Ueno, H,; Yoshida, M.; Nishiyama, M. J. Chem. Soc., Perkin Trans. 2 Submitted for publication.
20. Schleyer, P. v. R. In Cage Hydrocarbons;
21. Olah, G. A., Ed.; Wiley-Interscience: New York, 1990; pp 1-38.
22. (a) Tobe, Y.; Fujii, T., Matsumoto, H.; Naemura, K.; Achiba, Y.; Wakabayashi, T. J. Am. Chem. Soc. 1996, 118, 2758-2759.
23. (b) Tobe, Y.; Matsumoto, H.; Naemura, K.; Achiba, Y.; Wakabayashi, T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1800-1802.
24. (c) Wakabayashi, T.; Kohno, M.; Achiba, Y.; Shiromaru, H.; Momose, T.; Shida, T.; Naemura, K.; Tobe, Y. J. Chem. Phys. 1997, 107, 4783-4687.
25. - in the negative mode ion cyclotron resonance mass spectrum: Rubin, Y.; Parker, T. C.; Pastor, S.; Jalisatgi, S.; Boulle, C.; Wilkins, C. L. Angew. Chem. In press.
26. 6 isomers, see: Cahill, P. A. Chem. Phys. Lett. 1996, 254, 257-262.
27. (a) Meier, M. S.; Weedon, B. R.; Spielmann, H. P. J. Am. Chem. Soc. 1996, 118, 11682-11683.
28. (b) Known as hexahalo derivatives: Birkett, P. R.; Hitchcock, P. B.; Kroto, H. W.; Taylor, R.; Walton, D. R. M. Nature (London) 1992, 357, 479-481.
29. Birkett, P. R.; Avent, A. G.; Darwish, A. D.; Kroto, H. W.; Taylor, R.; Walton, D. R. M. J. Chem. Soc., Chem. Commun. 1993, 1230-1232.
30. (a) Armitage, J. B.; Entwistle, N.; Jones, E. R. H.; Whiting, M. C. J. Chem. Soc. 1954, 147-154.
31. (b) Johnson, T. R.; Walton, D. R. M. Tetrahedron 1972, 28, 5221-5236.
32. Haley, M. M.; Langsdorf, B. L. Chem. Commun. 1997, 1121-1122.
33. Cai, C.; Vasella, A. HelV. Chim. Acta 1995, 78, 2053-2064.
34. 3h) are conceivable, none of which was separated.
35. (a) Wurz, P.; Lykke, K. R. J. Phys. Chem. 1992, 96, 10129-10139.
36. (b) Christian, J. F.; Wan, Z.; Anderson, S. L. J. Phys. Chem. 1992, 96, 3574-3576.
37. (c) Wakabayashi, T.; Shiromaru, H.; Suzuki, S.; Kikuchi, K.; Achiba, Y. Surf. ReV. Lett. 1996, 3, 793-798.
38. Mitzner, R.; Campbell, E. E. B. J. Chem. Phys. 1995, 103, 2445-2453.
39. Kaizu, K.; Kohno, M.; Suzuki, S.; Shiromaru, H.; Moriwaki, T.; Achiba, Y. J. Chem. Phys. 1997, 106, 9954-9956.
40. Photolysis of 3 in benzene solution with a low-pressure mercury lamp resulted in the formation of indan (ca. 50% yield by 1H NMR spectrum) and uncharacterized polymeric materials. So far we are not able to perform flash vacuum pyrolysis of 3 owing to its low volatility. Further work in the preparative scale fragmentation of 3 is under way.