Synthesis and spectroscopic characterization of the first symmetrically and nonsymmetrically substituted fluorinated emerald-green trannulenes C 60F15R3 soluble in polar media and water

European Journal of Organic Chemistry

Volumn , Issue 6, 2010, Pages 1037-1045

  Troshin, Pavel A ^a   Khakina, Ekaterina A ^a   Zhilenkov, Alexander V ^a   Peregudov, Alexander S ^b   Troshina, Olesya A ^a   Kozlovskii, Viacheslav I ^c   Polyakova, Natalya V ^d   Lyubovskaya, Rimma N ^a  

^a INSTITUTE OF PROBLEMS OF CHEMICAL PHYSICS   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

^c SEMENOV INSTITUTE OF CHEMICAL PHYSICS   (Russian Federation)

^d Research Institute of Electrocarbon Products   (Russian Federation)

Author keywords

Annulenes; Bioorganic chemistry; Fluorine; Fullerenes

Indexed keywords

EID: 76449100372     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200901169     Document Type: Article

References (29)

1. a) J. Chandrasekhar, E. D. Jemmis, P. von Rague Schleyer, Tetrahedron Lett. 1979, 39, 3707;
2. b) P. von Rague Schleyer, H. Jiao, M. N. Glukhovtsev, J. Chandrasekhar, E. Kraka, J. Am. Chem. Soc. 1994, 116, 10129;
3. c) A.A. Fokin, H. Jiao, P. von Rague Schleyer, J. Am, Chem. Soc. 1998, 120, 9364.
4. G. A. Burley, Angew. Chem. Int. Ed. 2005, 44, 3176.
5. a) X. W. Wei, A. D. Darwish, O. Boltalina, P. B. Hitchcock, J. M. Street, R. Taylor, Angew. Chem. Int. Ed. 2001, 40, 2989;
6. b) G. A. Burley, A. G. Avent, O. V. Boltalina, T. Drewello, I. V. Gold't, M. Marcaccio, F'. Paolucci, D. Paolucci, J. M. Street, R. Taylor, Org. Biomol. Chem. 2003, 1, 2015;
7. c) G. A. Burley, A. G. Avent, I. V. Gol'dt, P. B. Hitchcock, H. Al-Matar, D. Paolucci, F. Paolucci, P. W. Fowler, A. Soncini, J. M. Street, R. Taylor, Org. Biomol. Chem. 2004, 2, 319;
8. d) A. D. Darwish, I. V. Kuvytchko, X.-W. Wei, O. V. Boltalina, I. V. Gol'dt, J. M. Street, R. Taylor, J. Chem. Soc. Perkin Trans. 2 2002, 1118;
9. e) X. W. Wei, A. Avent, O. Boltalina, A.D. Darwish, P.W. Fowler, J. P. B. Sandall, J. M. Street, R. Taylor, J. Chem. Soc. Perkin Trans. 2 2002, 41.
10. a) P. Troshin, R. N. Lyubovskaya, I. N. Ioffe, N B. Shustova, E. Kemnitz, S. I. Troyanov, Angew. Chem. 2005, 117, 238;
11. Angew. Chem. Int. Ed. 2005, 44, 234;
12. b) T. Canteenwala, P.A. Padmawar, L. Y. Chiang, J. Am. Chem. Soc. 2005, 127, 26.
13. a) G.A. Burley, A. G. Avent, O. V. Boltalina, I.V. Gol'dt, D. M. Guldi, M. Marcaccio, F. Paolucci, D. Paolucci, R. Taylor, Chem. Commun. 2003, 148;
14. b) D. M. Guldi, M. Marcaccio, F. Paolucci, D. Paolucci, J. Ramey, R. Taylor, G. A. Burley, J. Phys. Chem. A 2005, 109, 9723.
15. O. V. Boltalina, B. de La Vaissière, A. Yu. Lukonin, P.W. Fowler, A. K. Abdul-Sada, J. M. Street, R. Taylor, J. Chem. Soc. Perkin Trans. 2 2001, 550;
16. O. Boltalina, J. H. Holloway, E. G. Hope, J. M. Street, R. Taylor, J. Chem. Soc. Perkin Trans. 2 1998, 1845;
17. B. W. Clare, D. L. Kepert, R. Taylor, Org. Biomol. Chem. 2003, 1, 3618.
18. J. W. Aborgast, C. S. Foote, J. Am. Chem. Soc. 1991, 113, 8886.
19. Y. Tabata, Y. Murakami, Y. Ikada, Fullerene. Sci. Technol. 1997, 5, 989.
20. a) D. M. Guldi, G. M. A. Rahman, V. Sgobba, C. EhIi, Chem. Soc. Rev. 2006, 35, 471;
21. b) D. Bonifazi, O. Enger, F. Diederich, Chem. Soc. Rev. 2007, 36, 390;
22. c) A. Mateo-Alonso, C. Sooambar, M. Prato, Org. Biomol. Chem. 2006, 4, 1629.
23. L. J. Wilson, Interface 1999, 8, 24;
24. K. A. Gonzales, L. J. Wilson, W. Wu, G. H. Nancollas, Bioorg. Med. Chem. 2002, 10, 1997.
25. P. Pitt, H. Berry, Postgrad. Med. J. 1991, 67, 323.
26. a) P. A. Troshin, A. B. Kornev, A. S. Peregudov, S. A. Baskakov, R. N. Lyubovskaya, J. Fluorine Chem. 2005, 126, 1559;
27. b) A. B. Kornev, P. A. Troshin, A. S. Peregudov, Z. I. Klinkina, N. V. Polyakova, R. N. Lyubovskaya, Mendeleev Commun. 2006, 157.
28. M. Brettreich, A. Hirsch, Tetrahedron Lett. 1998, 39, 2731.
29. M. Yamamoto, K. Ichinose, N. Ishii, T. Khoji, K. Akiyoshi, N. Moriguchi, J. Sunamoto, T. Kanematsu, Oncol. Rep. 2000, 7, 107.