A tetrathiafulvalene-functionalized radiaannulene with multiple redox states

Angewandte Chemie - International Edition

Volumn 51, Issue 25, 2012, Pages 6099-6102

  Lincke, Kasper ^a   Floor Frellsen, Anders ^a   Parker, Christian Richard ^a   Bond, Andrew D ^b   Hammerich, Ole ^a   Brøndsted Nielsen, Mogens ^a  

^a UNIVERSITY OF COPENHAGEN   (Denmark)

^b UNIVERSITY OF SOUTHERN DENMARK   (Denmark)

Author keywords

alkynes; annulenes; aromaticity; redox chemistry; synthetic methods

Indexed keywords

ALKYNES; ANNULENES; AROMATICITIES; REDOX CHEMISTRY; SYNTHETIC METHODS;

CATALYSIS; CHEMISTRY;

ACETYLENE;

EID: 84862703020     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201202324     Document Type: Article

References (35)

1. F. Mitzel, C. Boudon, J.-P. Gisselbrecht, P. Seiler, M. Gross, F. Diederich, Helv. Chim. Acta 2004, 87, 1130-1157
2. G. Chen, L. Wang, D. W. Thompson, Y. Zhao, Org. Lett. 2008, 10, 657-660
3. G. Chen, L. Dawe, L. Wang, Y. Zhao, Org. Lett. 2009, 11, 2736-2739
4. M. Gholami, M. N. Chaur, M. Wilde, M. J. Ferguson, R. McDonald, L. Echegoyen, R. R. Tykwinski, Chem. Commun. 2009, 3038-3040
5. Y.-L. Wu, F. Bures, P. D. Jarowski, W. B. Schweizer, C. Boudon, J.-P. Gisselbrecht, F. Diederich, Chem. Eur. J. 2010, 16, 9592-9605.
6. H. Hopf, G. Maas, Angew. Chem. 1992, 104, 953-977
7. Angew. Chem. Int. Ed. Engl. 1992, 31, 931-954.
8. E. L. Spitler, C. A. Johnson II, M. M. Haley, Chem. Rev. 2006, 106, 5344-5386.
9. For a discussion of Wurster and Weitz systems, see:, K. Deuchert, S. Hünig, Angew. Chem. 1978, 90, 927-938
10. Angew. Chem. Int. Ed. Engl. 1978, 17, 875-886.
11. Y. Kuwatani, I. Ueda, Angew. Chem. 1995, 107, 2017-2019
12. Angew. Chem. Int. Ed. Engl. 1995, 34, 1892-1894.
13. M. R. Bryce, J. Mater. Chem. 2000, 10, 589-598
14. J. L. Segura, N. Martín, Angew. Chem. 2001, 113, 1416-1455
15. Angew. Chem. Int. Ed. 2001, 40, 1372-1409
16. D. Jérome, Chem. Rev. 2004, 104, 5565-5591
17. D. Canevet, M. Sallé, G. X. Zhang, D. Zhang, D. Zhu, Chem. Commun. 2009, 2245-2269
18. M. Hasegawa, M. Iyoda, Chem. Soc. Rev. 2010, 39, 2420-2427.
19. For a computational study on the aromaticity of TTF cations, see:, M. B. Nielsen, S. P. A. Sauer, Chem. Phys. Lett. 2008, 453, 136-139.
20. J. Anthony, A. M. Boldi, Y. Rubin, M. Hobi, V. Gramlich, C. B. Knobler, P. Seiler, F. Diederich, Helv. Chim. Acta 1995, 78, 13-45.
21. J.-P. Gisselbrecht, N. N. P. Moonen, C. Boudon, M. B. Nielsen, F. Diederich, Eur. J. Org. Chem. 2004, 2959-2972
22. M. B. Nielsen, F. Diederich, Chem. Rev. 2005, 105, 1837-1867.
23. M. J. Frisch et al., Gaussian 09, Gaussian, Inc., Wallingford CT, 2010. Complete reference: see the Supporting information.
24. M. B. Robin, P. Day, Adv. Inorg. Chem. Radiochem. 1968, 10, 247-422.
25. V. D. Parker, M. Tilset, O. Hammerich, J. Am. Chem. Soc. 1987, 109, 7905-7906.
26. K. Lahlil, A. Moradpour, C. Bowlas, F. Menou, P. Cassoux, J. Bonvoisin, J.-P. Launay, G. Dive, D. Dehareng, J. Am. Chem. Soc. 1995, 117, 9995-10002
27. H. Spanggaard, J. Prehn, M. B. Nielsen, E. Levillain, M. Allain, J. Becher, J. Am. Chem. Soc. 2000, 122, 9486-9494
28. J. Lyskawa, M. Sallé, J.-Y. Balandier, F. Le Derf, E. Levillain, M. Alain, P. Viel, S. Palacin, Chem. Commun. 2006, 2233-2235
29. I. Aprahamian, J.-C. Olsen, A. Trabolsi, J. F. Stoddart, Chem. Eur. J. 2008, 14, 3889-3895
30. M. Hasegawa, Y. Kobayashi, K. Hara, H. Enozawa, M. Iyoda, Heterocycles 2009, 77, 837-842
31. A. Vacher, F. Barrière, T. Roisnel, L. Piekera-Sady, D. Lorcy, Organometallics 2011, 30, 3570-3578.
32. Y. N. Kreicberga, O. Y. Neilands, Zh. Org. Khim. 1985, 21, 2009-2010
33. C. A. Christensen, L. M. Goldenberg, M. R. Bryce, J. Becher, Chem. Commun. 2000, 331-332
34. V. Khodorkovsky, L. Shapiro, P. Krief, A. Shames, G. Mabon, A. Gorgues, M. Giffard, Chem. Commun. 2001, 2736-2737.
35. P. von R. Schleyer, C. Maerker, A. Drandfeld, H. Jiao, N. J. R. v. E. Hommes, J. Am. Chem. Soc. 1996, 118, 6317-6318.