The synthesis of hexafluorosumanene and its congeners

Chemistry - A European Journal

Volumn 19, Issue 10, 2013, Pages 3282-3286

  Schmidt, Bernd M ^a,c   Topolinski, Berit ^a,c   Higashibayashi, Shuhei ^a   Kojima, Tatsuhiro ^b   Kawano, Masaki ^b   Lentz, Dieter ^c   Sakurai, Hidehiro ^a  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b Pohang University of Science and Technology (POSTECH)   (South Korea)

^c FREIE UNIVERSITÄT BERLIN   (Germany)

Author keywords

buckybowls; crystal engineering; fluorine; pi interactions; sumanene

Indexed keywords

BUCKYBOWLS; CATHODIC SHIFTS; COLUMNAR STRUCTURES; ELECTRON-WITHDRAWING SUBSTITUENTS; PI INTERACTIONS; REDUCTION POTENTIAL; SUMANENE; SYNTHESISED;

CHEMISTRY; CRYSTAL ENGINEERING; SYNTHESIS (CHEMICAL);

FLUORINE;

EID: 84874422588     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201204622     Document Type: Article

References (42)

1. B. M. Schmidt, B. Topolinski, P. Roesch, D. Lentz, Chem. Commun. 2012, 48, 6520-6522
2. B. Topolinski, B. M. Schmidt, M. Kathan, S. I. Troyanov, D. Lentz, Chem. Commun. 2012, 48, 6298-6300.
3. Y.-T. Wu, D. Bandera, R. Maag, A. Linden, K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 2008, 130, 10729-10739
4. A. S. Filatov, E. A. Jackson, L. T. Scott, M. A. Petrukhina, Angew. Chem. 2009, 121, 8625-8628
5. Angew. Chem. Int. Ed. 2009, 48, 8473-8476
6. A. S. Filatov, L. T. Scott, M. A. Petrukhina, Cryst. Growth Des. 2010, 10, 4607-4621, and references therein.
7. D. Lentz, B. M. Schmidt, H. Sakurai, Abstr. Pap. 242nd ACS National Meeting & Exposition (Denver, CO) 2011, p. FLUO-66
8. B. M. Schmidt, S. Seki, B. Topolinski, K. Ohkubo, S. Fukuzumi, H. Sakurai, D. Lentz, Angew. Chem. 2012, 124, 11548-11551
9. 5, has been reported by others recently
10. I. V. Kuvychko, S. N. Spisak, Y.-S. Chen, A. A. Popov, M. A. Petrukhina, S. H. Strauss, O. V. Boltalina, Angew. Chem. 2012, 124, 5023-5026
11. Angew. Chem. Int. Ed. 2012, 51, 4939-4942.
12. T. Amaya, S. Seki, T. Moriuchi, K. Nakamoto, T. Nakata, H. Sakane, A. Saeki, S. Tagawa, T. Hirao, J. Am. Chem. Soc. 2009, 131, 408-409
13. S. Higashibayashi, R. Tsuruoka, Y. Soujanya, U. Purushotham, G. N. Sastry, S. Seki, T. Ishikawa, S. Toyota, H. Sakurai, Bull. Chem. Soc. Jpn. 2012, 85, 450-467.
14. L. Zoppi, L. Martin-Samos, K. K. Baldridge, J. Am. Chem. Soc. 2011, 133, 14002-14009.
15. Y. Morita, S. Nakao, S. Haesuwannakij, S. Higashibayashi, H. Sakurai, Chem. Commun. 2012, 48, 9050-9052.
16. T. Amaya, K. Mori, H.-L. Wu, S. Ishida, J.-i. Nakamura, K. Murata, T. Hirao, Chem. Commun. 2007, 1902-1904
17. T. Amaya, T. Nakata, T. Hirao, J. Am. Chem. Soc. 2009, 131, 10810-10811
18. S. Higashibayashi, R. B. Nasir Baig, Y. Morita, H. Sakurai, Chem. Lett. 2012, 41, 84-86
19. S. Higashibayashi, H. Sakurai, J. Am. Chem. Soc. 2008, 130, 8592-8593
20. S. Higashibayashi, H. Sakurai, Chem. Lett. 2011, 40, 122-128
21. H. Sakurai, T. Daiko, H. Sakane, T. Amaya, T. Hirao, J. Am. Chem. Soc. 2005, 127, 11580-11581
22. Q. Tan, S. Higashibayashi, S. Karanjit, H. Sakurai, Nat. Commun. 2012, 3, 891.
23. S. Mebs, M. Weber, P. Luger, B. M. Schmidt, H. Sakurai, S. Higashibayashi, S. Onogi, D. Lentz, Org. Biomol. Chem. 2012, 10, 2218-2222.
24. R. Tsuruoka, S. Higashibayashi, T. Ishikawa, S. Toyota, H. Sakurai, Chem. Lett. 2010, 39, 646-647
25. T. Amaya, M. Hifumi, M. Okada, Y. Shimizu, T. Moriuchi, K. Segawa, Y. Ando, T. Hirao, J. Org. Chem. 2011, 76, 8049-8052
26. E. Cauët, D. Jacquemin, Chem. Phys. Lett. 2012, 519-520, 49-53.
27. W. B. Motherwell, J. A. Wilkinson, Synlett 1991, 1991, 191-192
28. T. Fuchigami, T. Fujita, J. Org. Chem. 1994, 59, 7190-7192
29. C. Ye, B. Twamley, J. M. Shreeve, Org. Lett. 2005, 7, 3961-3964; for a recent review see
30. V. Hugenberg, G. Haufe, J. Fluorine Chem. 2012, 143, 238-262.
31. S. C. Sondej, J. A. Katzenellenbogen, J. Org. Chem. 1986, 51, 3508-3513
32. Y. Ie, M. Nitani, Y. Aso, Chem. Lett. 2007, 36, 1326-1327
33. V. Hugenberg, R. Fröhlich, G. Haufe, Org. Biomol. Chem. 2010, 8, 5682-5691.
34. R. D. Chambers, G. Sandford, M. Atherton, J. Chem. Soc. Chem. Commun. 1995, 177
35. R. D. Chambers, G. Sandford, M. E. Sparrowhawk, M. J. Atherton, J. Chem. Soc. Perkin Trans. 1 1996, 1941-1944.
36. 2 was 0.986.
37. T. Amaya, H. Sakane, T. Muneishi, T. Hirao, Chem. Commun. 2008, 765-767; two hexasubstituted sumanenes were reported, in which a low inversion barrier was observed, corresponding to a shallow bowl depth.
38. L. Farrugia, J. Appl. Crystallogr. 1997, 30, 565.
39. Persistence of Vision Pty. Ltd. http://povray.org/.
40. Gaussian 03 (Revision D.01), M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian, Inc., Wallingford CT, 2004.
41. H.-J. Schneider, Chem. Sci. 2012, 3, 1381-1394.
42. H. Suezawa, T. Yoshida, S. Ishihara, Y. Umezawa, M. Nishio, CrystEngComm 2003, 5, 514-518.