Abstract
The synthesis of Schiff base macrocycles in the absence of templating cations and in non-protic and non-coordinating solvent media is reported. The reaction of pyridine-2,6-dicarboxaldehyde with the diamines 1,2-bis(2-aminophenoxy) ethane and 1,4-bis(2-aminophenoxy) butane has been found to give the corresponding macrobicyclic aminals. The chemical properties of the aminals are reported together with a preliminary study of their metal complexation reactions. The X-ray crystal structure of the aminal derived from pyridine-2,6-dicarboxaldehyde and 1,2-bis(2-aminophenoxy) ethane has been determined and verifies the macrobicyclic nature of the product.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
R. W. Layer:Chem. Rev. 63, 489 (1963).
S. M. Nelson, C. V. Knox, M. McCann and M. G. B. Drew:J. Chem. Soc., Dalton Trans. 1669 (1981).
V. Katovic, L. T. Taylor and D. H. Busch:Inorg. Chem. 10, 458 (1971).
D. H. Cook and D. E. Fenton:Inorg. Chim. Acta 25, L95 (1977).
P. Moore, N. W. Alcock, R. G. Kingston and C. Pierpoint:J. Chem. Soc., Dalton Trans. 1941 (1989).
A. Bashall, D. E. Fenton, A. J. Leong, L. F. Lindoy, M. McPartlin, B. P. Murphy and P. A. Tasker:J. Chem. Soc., Dalton Trans. 2543 (1987).
International Tables for X-ray Crystallography, Vol. 4, Kynoch Press, Birmingham (1974), distr. Kluwer Academic Publishers, Dordrecht, the Netherlands.
G. M. Sheldrick:SHELXTL, An integrated system for solving, refining and displaying crystal structures from diffraction data (Revision 4), University of Göttingen, F.R. Germany 1983).
H. Adams, N. A. Bailey, D. E. Fenton, P. D. Hempstead, B. A. Hewes, S. J. Kitchen, and M. J. Winter:Polyhedron 8, 1857 (1989).
P. Tasker, N. W. Alcock, D. C. Liles and M. McPartlin:J. Chem. Soc., Chem Commun. 727 (1974).
Author information
Authors and Affiliations
Additional information
This paper is dedicated to the memory of the late Dr C. J. Pedersen.
Rights and permissions
About this article
Cite this article
Atkinson, A., Bailey, N.A., Fenton, D.E. et al. Macrobicyclic aminals. J Incl Phenom Macrocycl Chem 12, 175–186 (1992). https://doi.org/10.1007/BF01053860
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01053860