Selective endo-Calix. Complexation of Linear Alkylammonium Cations by Functionalized (1,3)-p-fer£-Butylcalix[5]crown Ethers

Journal of Organic Chemistry

Volumn 61, Issue 25, 1996, Pages 8724-8725

  Pappalardo, Sebastiane ^a,b   Parisi, Melchiorre F ^a,b  

^a UNIVERSITY OF CATANIA   (Italy)

^b UNIVERSITY OF MESSINA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001343509     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9615108     Document Type: Article

References (13)

1. Diederich, F. Cyclophanes; Royal Society of Chemistry: Cambridge, 1991.
2. Gutsche, C. D. Calixarenes; Stoddart, J. F., Ed.; Monographs in Supramolecular Chemistry; The Royal Society of Chemistry: Cambridge, 1989; Vol. 1. Calixarenes, a Versatile Class of Macrocyclic Compounds', Vicens, J., Böhmer, V., Eds.; Kluwer: Dordrecht, 1991. Böhmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713.
3. Previously, Gutsche et al. postulated the formation of an endocomplex, from the interaction ofp-allylcalix[4]arene with -BuNH2, on the basis of a 2D NOE spectrum: Gutsche, C. D.; Iqbal, M.; Alam, I. J. Am. Chem. Soc. 1987, 709, 4314.
4. Kraft, D.; Arnecke, R.; Böhmer, V.; Vogt, W. Tetrahedron 1993, 49, 6019.
5. Stewart, D. R.; Gutsche, C. D. Org. Prep. Proc. Int. 1993, 25, 137.
6. Kyba, E. P.; Gokel, G. W.; de Jong, F.; Koga, K.; Sousa, L. R.; Siegel, M. G.; Kaplan, L.; Sogah, G. D. Y.; Cram, D. J. J. Org. Chem. 1977, 42, 4173.
7. Experimental procedures and characterization data for all new compounds are shown in the Supporting Information.
8. Stewart, D. R.; Krawiec, M.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. J. Am. Chem. Soc. 1995, 117, 586.
9. Jaime, C.; de Mendoza, J.; Prados, P.; Nieto, P. M.; Sanchez, C. J. Org. Chem. 1991, 56, 3372.
10. Lehn, J.-M. Angew. Chem., Int. Ed. Engl. 1988, 27, 89. Cram, D. J. Angew. Chem., Int. Ed. Engl. 1988, 27, 1009.
11. 12 of the "isolated" picolyl substituent, which is almost completely protonated even by 1 equiv of L-Phe-OMe-HCl, is believed to be associated with the juxtaposition of the polyether bridge that stabilizes the Pyridinium cation by self-complexation. Subsequent to protonation, compound 2e assumes a more open cone conformation, as suggested by the resonance of the "isolated" p-tert-bulyl substituent, which is shifted downfield (Δδ5 0.95 ppm)..
12. 3+) = 3.3.
13. Araki, K.; Hashimoto, N.; Otsuka, H.; Shinkai, S. J. Org. Chem. 1993,58, 5958. Han, S.-Y.; Kang, M.-H.; Jung, Y.-E.; Chang, S.-K. J. Chem. Soc., Perkin Trans. 2 1994, 835. Kubo, Y.; Maruyama, S.; Ohhara, N.; Nakamura, M.; Tokita, S. J. Chem. Soc., Chem. Commun. 1995, 1727 and references cited therein.