Synthesis and Anion-Selective Complexation of Cyclophane-Based Cyclic Thioureas

Journal of Organic Chemistry

Volumn 65, Issue 2, 2000, Pages

  Sasaki, Shin Ichi ^a,b   Mizuno, Masaaki ^b   Naemura, Koichiro ^b   Tobe, Yoshito ^b  

^a KEIO UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0345850147     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (12)

1. For reviews of synthetic anion receptors: (a) Scheerder, J.; Engbersen, J. F. J.; Reinhoudt, D. N. Red. Trav. Chim. Pays-Bas 1996, 115, 307-320. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646. Antonisse, M. M. G.; Reinhoudt, D. N. Chem. Commun. 1998, 443-448.
2. For reviews of synthetic anion receptors: (a) Scheerder, J.; Engbersen, J. F. J.; Reinhoudt, D. N. Red. Trav. Chim. Pays-Bas 1996, 115, 307-320. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646. Antonisse, M. M. G.; Reinhoudt, D. N. Chem. Commun. 1998, 443-448.
3. For reviews of synthetic anion receptors: (a) Scheerder, J.; Engbersen, J. F. J.; Reinhoudt, D. N. Red. Trav. Chim. Pays-Bas 1996, 115, 307-320. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609-1646. Antonisse, M. M. G.; Reinhoudt, D. N. Chem. Commun. 1998, 443-448.
4. For reviews of ion-selective electrodes and optodes: Bühlmann, P.; Pretsch, E.; Bakker, E. Chem. Rev. 1998, 98, 1593-1687.
5. In some cases, weaker anion binding ability of thiourea-based receptors than that of the corresponding urea-based receptors is observed due to the competing intramolecular hydrogen bonding of thiourea groups: (a) Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815-7820. (b) Raposo, C.; Almaraz, M.; Martín, M.; Weinrich, V.; Mussóns, M. L.; Alcázar, V.; Caballero, M. C.; Morán, J. R. Chem. Lett. 1995, 759-760.
6. In some cases, weaker anion binding ability of thiourea-based receptors than that of the corresponding urea-based receptors is observed due to the competing intramolecular hydrogen bonding of thiourea groups: (a) Scheerder, J.; Fochi, M.; Engbersen, J. F. J.; Reinhoudt, D. N. J. Org. Chem. 1994, 59, 7815-7820. (b) Raposo, C.; Almaraz, M.; Martín, M.; Weinrich, V.; Mussóns, M. L.; Alcázar, V.; Caballero, M. C.; Morán, J. R. Chem. Lett. 1995, 759-760.
7. Bordwell, F. G.; Algrim, D. J.; Harrelson, J. A., Jr. J. Am. Chem. Soc. 1988, 110, 5904-5906.
8. For substituent effects on association constants of arylthioureas: Wilcox, C. S.; Kim, E.; Romano, D.; Kuo, L. H.; Burt, A. L.; Curran, D. P. Tetrahedron 1995, 51, 621-634.
9. Bühlmann, P.; Nishizawa, S.; Xiao, K. P.; Umezawa, Y. Tetrahedron 1997, 53, 1647-1654.
10. (a) Fan, E.; Van Arman, S. A.; Kincaid, S.; Hamilton, A. D. J. Am. Chem. Soc. 1993, 115, 369-370.
11. (b) Nishizawa, S.; Bühlmann, P.; Iwao, M.; Umezawa, Y. Tetrahedron Lett. 1995, 36, 6483-6486.
12. Scheerder, J.; Engbersen, J. F. F.; Casnati, A.; Ungaro, R.; Reinhoudt, D. N. J. Org. Chem. 1995, 60, 6448-6454.