[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/bkcs.2002.23.11.1629

Conformations of Tetrahomodioxa-p0phenylcalix[4]arene Alkyl Ethers

Publication Information

Bulletin of the Korean Chemical Society / v.23, no.11, 2002 , pp. 1629-1634 More about this Journal

Abstract

Reaction of tetrahomodioxa p-phenylcalix[4]arene with alkyl halide and NaH in DMF leads to the title tetra-alkylated derivatives, 7,13,21,27-tetra-phenyl-29,30,31,32-tetraalkyloxy-2,3,16,17-tetrahomo-3,17-dioxacalix [4]arenes, their preferred conformations were determined by NMR spectra as C-1,2-alternate. The molecular structure of allyl derivative has been solved by X-ray diffraction methods. The molecules have a conformation with pseudo center of symmetry. The benzene ring A is up, ring C is down, B and D rings are flat with respect to the plane of the macrocyclic ring.

Keywords

Homooxacalix[4]arene; Conformation; Crystal structure;

Citations & Related Records

Times Cited By Web Of Science : 1 (Related Records In Web of Science)
Times Cited By SCOPUS : 1

Reference
Cited By SCOPUS

1	Calixarenes: A Versatile Class of Macrocyclic Compounds; Vicens, J., Bohmer, V., Eds.: Kluwer: Dordrecht, 1991.
2	Bohmer, V. Angew. Chem., Int. Ed. Engl. 1995, 34, 713. DOI ScienceOn
3	Gutsche, C. D.; Dhawan, B.; No, K. H.; Muthukrishnan, R. J. Am. Chem. Soc. 1981, 103, 3782. DOI
4	Thuery, P.; Nierlich, M.; Vicens, J.; Masci, B. Acta Cryst. 2001, C57, 70.
5	Felix, S.; Ascenso, J. R.; Lamartine, R.; Pereira, J. L. C. Syn. Commun. 1998, 28, 1793. DOI ScienceOn
6	Dhawan, B.; Gutsche, C. D. J. Org. Chem. 1983, 48, 1536. DOI
7	No, K.; Kim, J. S.; Shon, O. J.; Yang, S. H.; Suh, I. H.; Kim, J. G.; Bartsch, R. A.; Kim, J. Y. J. Org. Chem. 2001, 66, 5976. DOI ScienceOn
8	Marcos, P. M.; Ascenso, J. R.; Lamartine, R.; Pereira, J. L. C. Tetrahedron 1997, 53, 11791. DOI ScienceOn
9	No, K. Bull. Korean Chem. Soc. 1999, 20, 33.
10	Jaime, C.; de Mendoza, J.; Prados, P.; Nieto, P. M.; Sanches, C. J. Org. Chem. 1991, 56, 3372. DOI
11	Gutsche, C. D.; No, K. J. Org. Chem. 1982, 47, 235.
12	Sheldrick, G. M. Shelxl-97, Program for Crystal Structure Determination; Institute für Anorganische Chemie der Univ.: Germany, 1997.
13	Johnson, C. K. ORTEP, Report-3794; Oak Ridge National Lab. Tennessee, U.S.A., 1975.
14	Harrowfield, J. M.; Ogden, M. I.; White, A. H. J. Chem. Soc., Dalton Trans. 1991, 979.
15	Gutsche, C. D. Calixarenes Revisited; Royal Society of Chemistry: Cambridge, 1998.
16	Bohmer, V.; McKervey, M. A. Chemie in unserer Zeit; 1991, 195.
17	Gutsche, C. D. Calixarenes, Monographs in Supramolecular Chemistry; Stoddart, J. F., Ed.; Royal Society of Chemistry: Cambridge, U. K., 1989; Vol. 1.
18	International Table for X-ray Crystallography; Kynoch Press: Birmingham, England, 1974; Vol. IV.
19	Thuery, P.; Nierlich, M.; Vicens, J.; Masci, B. Acta Cryst. 2001, C57, 70.
20	Thuery, P.; Nierlich, M.; Vicens, J.; Masci, B. Acta Cryst. 2001, C57, 833.
21	No, K.; Park, Y. J.; Choi, E. J. Bull. Korean Chem. Soc. 1999, 20, 905.
22	Bavoux, C.; Vocanson, F.; Perrin, M.; Lamartine, R. J. Incl. Phenom. Mol. Recogn. Chem. 1995, 22, 119. DOI
23	Gutsche, C. D. In Synthesis of Macrocycles: Design of Selective Complexing Agents; Izatt, R. M.; Christensen, J. J., Eds.; Wiley: New York, 1987; p 93.
24	Masci, B.; Gcbrielli, M.; Morfera, S. L.; Nierlich, M.; Thuery, P. Polyhedron 2002, 21, 1125. DOI ScienceOn
25	Gutsche, C. D. Calixarenes; Royal Society of Chemistry: Cambridge, 1989.
26	Ungaro, R.; Pochini, A. In Frontiers in Supramolecular Organic Chemistry and Photochemistry; Schneider, H.-J., Ed.; VCH: Weinheim, Germany, 1991; pp 57-81.
27	Kim, J. S.; Lee, W. K.; Kim, J. G.; Suh, I. H.; Yoon, J. Y.; Lee, J. H. J. Org. Chem. 2000, 65, 7215. DOI ScienceOn
28	Stewart, D. R.; Krawiee, M.; Kashyap, R. P.; Watson, W. H.; Gutsche, C. D. J. Am. Chem. Soc. 1995, 117, 586. DOI ScienceOn
29	Iwamoto, K.; Araki, K.; Shinkai, S. Tetrahedron 1991, 47, 4325. DOI ScienceOn
30	Van Loon, J.-D.; Verboom, W.; Reinhoudt, D. N. Org. Prep. Proc. Int. 1992, 24, 437-462. DOI ScienceOn
31	Masci, B.; Saccheo, S. Tetrahedron Lett. 1993, 49, 10739. DOI ScienceOn
32	Asfari, Z.; Harrowfield, J. M.; Ogden, M. I.; Vicens, J.; White, A. H. Angew. Chem., Int. Ed. Engl. 1991, 30, 854. DOI
33	Gutsche, C. D. In Inclusion Compounds; Atwood, J. L., Davies, J. E. D., MacNicol, D. D.; Eds.; Oxford University Press: New York, 1991; Vol. 4, pp 27-63.