Novel Syntheses of Three C30H12 Bowl-Shaped Polycyclic Aromatic Hydrocarbons

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 4, 1997, Pages 406-408

  Hagen, Stefan ^a   Bratcher, Matthew S ^a   Erickson, Mark S ^b   Zimmermann, Gerhard ^c   Scott, Lawrence T ^a  

^a BOSTON COLLEGE   (United States)

^b UNIVERSITY OF MISSISSIPPI   (United States)

^c UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

Fullerenes; Hydrocarbons; Polycycles; Pyrolysis

Indexed keywords

EID: 0030971918     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199704061     Document Type: Article

References (23)

1. For recent reviews on bowl-shaped fullerene subunits see a) J. S. Siegel, T. J. Seiders, Chem. Br. 1995, 313-316;
2. b) R. Faust, Angew. Chem. 1995, 107, 1562-1564; Angew. Chem. Int. Ed. Engl. 1995, 34, 1429-1432;
3. b) R. Faust, Angew. Chem. 1995, 107, 1562-1564; Angew. Chem. Int. Ed. Engl. 1995, 34, 1429-1432;
4. c) P. W. Rabideau, A. Sygula in Adv. Theor. Interesting Mol., Vol. 3 (Ed.: R. P. Thummel), JAI, Greenwich, 1995, pp. 1-36;
5. d) Acc. Chem. Res. 1996, 29, 235-242.
6. a) L. T. Scott, M. M. Hashemi, D. T. Meyer, H. B. Warren, J. Am. Chem. Soc. 1991, 113, 7082-7084;
7. b) L. T. Scott, Pure Appl. Chem. 1996, 68, 291-300.
8. The systematic IUPAC names are benz[5,6-as]indaceno[3,2,1,8,7-mnopqr]indeno[4,3,2,1-cdef]chrysene (1), diacenaphtho[3,2,1,8-cdefg;3′,2′,1′,8′-lmnop]-chrysene (2), and difluoreno[2,1,9,8,7-defghi;2′,1′,9′,8′,7′-mnopqr] naphthacene (3).
9. P. W. Rabideau, A. H. Abdourazak, H. Folsom, J. Am. Chem. Soc. 1994, 116, 7891-7892.
10. A. H. Abdourazak, Z. Marcinow, A. Sygula, R. Sygula, P. W. Rabideau, J. Am. Chem. Soc. 1995, 117, 6410-6411.
11. T. Wakabayashi, K. Kikuchi, S. Suzuki, H. Shiromaru, Y. Achiba, J. Phys. Chem. 1994, 98, 3090-3091 and ref. cited therein.
12. S. Hagen, L. T. Scott, J. Org. Chem. 1996, 61, 7198-7199.
13. a) R. Faust, K. P. C. Vollhardt, Seventh International Symposium on Novel Aromatic Compounds (Victoria, B. C., Canada), poster no. 61, 1992. For related work, see
14. b) G. Mehta, G. V. Sharma, M. A. Kumar, T. V. Vedavyasa, E. D. Jemmis, J. Chem. Soc. Perkin Trans. I 1995, 2529-2530.
15. S. Hagen, U. Nuechter, M. Nuechter, G. Zimmermann, Polycyclic Aromat. Compd. 1995, 4, 209-217.
16. L. T. Scott, M. S. Bratcher, S. Hagen, J. Am. Chem. Soc. 1996, 118, 8743-8744.
17. 2 see M. J. Plater, Tetrahedron Lett. 1994, 35, 6147-6150; M. Sarobe, L. W. Jenneskens, U. Wiersum, ibid 1996, 37, 1121-1122.
18. 2 see M. J. Plater, Tetrahedron Lett. 1994, 35, 6147-6150; M. Sarobe, L. W. Jenneskens, U. Wiersum, ibid 1996, 37, 1121-1122.
19. 1H NMR spectrum confirms the presence of three equivalent fjord region hydrogen atoms with no neighboring hydrogens in 5.
20. FVP were conducted as described in ref. [10].
21. 2S, HCl, ethanol; c) tetrahydronaphthalene, 207°C, 10 min, 19% for steps b +c. The serendipitous synthesis of 6, its structure elucidation by spectroscopic methods, and its X-ray crystal structure have been described in detail: S. Hagen, Ph.D. Dissertation, Universität Leipzig, 1995.
22. S. Hagen, U. Nuechter, M. Nuechter, G. Zimmermann, Tetrahedron Lett. 1994, 35, 7013-7014.
23. 12): calcd: 372.0939, found: 372.0939.