BF2 complexes of β-tetraethyl-substituted dipyrrolyldiketones as anion receptors: Potential building subunits for oligomeric systems

Journal of Organic Chemistry

Volumn 72, Issue 7, 2007, Pages 2612-2616

  Maeda, Hiromitsu ^a,b   Kusunose, Yukio ^a   Mihashi, Yuta ^a   Mizoguchi, Tadashi ^a  

^a RITSUMEIKAN UNIVERSITY   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANION BINDING; ANION RECEPTORS; ETHOXYCARBONYL MOIETIES; STERICAL REPULSION;

COMPLEXATION; NEGATIVE IONS; POLARIZATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

KETONES;

1,3 DIPYRROLYL 1,3 PROPANEDIONE DERIVATIVE; ANION; CARBONYL DERIVATIVE; KETONE DERIVATIVE; OLIGOMER; PYRROLIDINE DERIVATIVE; UNCLASSIFIED DRUG; BORON DERIVATIVE; ETHYLENE; ETHYLENE DERIVATIVE; KETONE; PYRROLE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE; TETRABUTYLAMMONIUM;

ARTICLE; BINDING AFFINITY; BINDING SITE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONFORMATION; ELECTRON TRANSPORT; GEL CHROMATOGRAPHY; POLARIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; PURIFICATION; REACTION ANALYSIS; STEREOSPECIFICITY; STRUCTURE ANALYSIS; SYNTHESIS; X RAY DIFFRACTION; CHEMISTRY; HYDROGEN BOND;

ANIONS; BORON COMPOUNDS; ETHYLENES; HYDROGEN BONDING; KETONES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PYRROLES; QUATERNARY AMMONIUM COMPOUNDS;

EID: 34047230469     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062660d     Document Type: Article

References (24)

1. (a) Supramolecular Chemistry of Anions; Bianchi, A., Bowman-James, K., Gracía-España, E., Eds.; Wiley-VCH: New York, 1997.
2. (b) Fundamentals and Applications of Anion Separations; Singh R. P., Moyer, B. A., Eds.; Kluwer Academic/Plenum Publishers: New York, 2004.
3. (c) Anion Sensing; Stibor, I., Ed.; Springer-Verlag: Berlin, Germany, 2005.
4. (d) Sessler, J. L.; Gale, P. A.; Cho, W.-S. Anion Receptor Chemistry; RSC: Cambridge, UK, 2006.
5. (a) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1515.
6. (b) Beer, P. D.; Gale, P. A. Angew. Chem., Int. Ed. 2001, 40, 487.
7. (c) Martínez-Mãnez, R.; Sancenón, F. Chem. Rev. 2003, 103, 4419.
8. (a) Gale, P. A.; Sessler, J. L.; Král, V. Chem. Commun. 1998, 1.
9. (b) Sessler, J. L.; Davis, J. Acc. Chem. Res. 2001, 34, 989.
10. (a) Maeda, H.; Kusunose, Y. Chem. Eur. J. 2005, 11, 5661.
11. (b) Fujimoto, C.; Kusunose, Y.; Maeda, H. J. Org. Chem. 2006, 71, 2389.
12. (c) Maeda, H.; Ito, Y. Inorg. Chem. 2006, 45, 8205.
13. (d) Maeda, H.; Ito, Y.; Kusunose, Y.; Nakanishi, T. Chem. Commun. 2007, in press (DOI: 10.1039/b615787d).
14. (e) Maeda, H.; Kusunose, Y.; Terasaki, M.; Ito, Y.; Fujimoto, C.; Fujii, R.; Nakanishi, T. Chem. Asian J. 2007, 2, 350.
15. Oddo, B.; Dainotti, C. Gazz. Chim. Ital. 1912, 42, 716.
16. Stark, W. M.; Baker, M. G.; Leeper, F. J.; Raithby, P. R.; Battersby, A. R. J. Chem. Soc., Perkin Trans. 1 1988, 1187.
17. Sessler, J. L.; Mozaffari, A.; Johnson, M. R. Org. Synth. 1992, 70, 68.
18. Sessler, J. L.; Berthon-Gelloz, G.; Gale, P. A.; Camiolo, S.; Anslyn, E. V.; Anzenbacher, P., Jr.; Furuta, H.; Kirkovits, G. J.; Lynch, V. M.; Maeda, H.; Morosini, P.; Scherer, M.; Shriver, J.; Zimmerman, R. S. Polyhedron 2003, 22, 2963.
19. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, (Revision C.01); Gaussian, Inc.: Wallingford, CT, 2004.
20. (a) Ishiyama, T.; Miyaura, N. J. Organomet. Chem. 2003, 680, 3.
21. (b) Ishiyama, T.; Takagi, J.; Yonekawa, Y.; Hartwig, H, F.; Miyaura, N. Adv. Synth. Catal. 2003, 345, 1103.
22. (c) Ishiyama, T.; Miyaura, N. Pure Appl. Chem. 2006, 78, 1369.
23. (a) Hata, H.; Shinokubo, H.; Osuka, A. J. Am. Chem. Soc. 2005, 127, 8264.
24. (b) Hiroto, S.; Hisaki, I.; Shinokubo, H.; Osuka, A. Angew. Chem., Int. Ed. 2005, 44, 6763.