Abstract
The formation of a stable calix[4]arene monohemiketal is described. X-ray crystallographic data provide conclusive evidence for the presence of a stabilizing hydrogen bond.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
C.D. Gutsche:Calixarenes. Monographs in Supramolecular Chemistry, Vol. 1; Ed. J.F. Stoddart; The Royal Society of Chemistry: Cambridge (1989).
J. Vicens and V. Böhmer (Eds.):Calixarenes: A Versatile Class of Macrocyclic Compounds, Kluwer Academic Publishers: Dordrecht (1991).
J.-D. van Loon, A. Arduini, L. Coppi, W. Verboom, A. Pochini, R. Ungaro, S. Harkema, and D.N. Reinhoudt:J. Org. Chem. 55, 5639 (1990).
P.A. Reddy and C.D. Gutsche:J. Org. Chem. 58, 3245 (1993).
A. Casnati, A. Comelli, M. Fabbi, V. Bocchi, G. Mori, F. Ugozzoli, A.M. Manotti Lanfredi, A. Pochini, and R. Ungaro:Recl. Trav. Chim. Pays-Bas 112, 384 (1993).
Y. Morita, T. Agawa, Y. Kai, N. Kanehisa, N. Kasai, E. Nomura, and H. Taniguchi:Chem. Lett. 1349 (1989).
Y. Morita, T. Agawa, E. Nomura, and H. Taniguchi:J. Org. Chem. 57, 3658 (1992).
K. Suga, M. Fujihara, Y. Morita, and T. Agawa:J. Chem. Soc., Faraday Trans. 87, 1575 (1991).
P.A. Reddy, R.P. Kashyap, W.H. Watson, and C.D. Gutsche:Isr. J. Chem. 32, 89 (1992).
O. Aleksiuk, F. Grynszpan, and S.E. Biali:J. Org. Chem. 58, 1994 (1993).
G. Germain, P. Main, and M.M. Woolfson:Acta Crystallogr. A 27, 368 (1971).
Structure Determination Package: B.A. Frenz and Associates, Inc., College Station, TX, and Enraf-Nonius, Delft (1983).
International Tables for X-ray Crystallography, Vol. IV; Kynoch Press: Birmingham, England (1974). Distr. Kluwer Academic Publishers. Dordrecht, the Netherlands.
W.D.S. Motherwell and W. Clegg:PLUTO. Program for plotting molecular and crystal structures, University of Cambridge, England (1978).
J.-D. van Loon, J.F. Heida, W. Verboom, and D.N. Reinhoudt:Recl. Trav. Chim. Pays-Bas 111, 353 (1992).
F. Ugozzoli and G.D. Andreetti:J. Incl. Phenom. 13, 337 (1992).
Y. Naruta and K. Maruyama:The Chemistry of Quinonoid Compounds Eds. S. Patai, Z. Rappoport; Wiley: Chichester (1988).
Author information
Authors and Affiliations
Additional information
Supplementary Data. Lists of H-atom parameters and bond lengths and angles involving hydrogens have been deposited with the British Library Document Supply Centre as Supplementary Publication No. SUP 82159 (5 pp.).
Rights and permissions
About this article
Cite this article
Timmerman, P., Harkema, S., Van Hummel, G.J. et al. Isolation and X-ray crystal structure of a stable calix[4]arene monohemiketal. J Incl Phenom Macrocycl Chem 16, 189–197 (1993). https://doi.org/10.1007/BF00709151
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF00709151