Abstract
Cyclocondensation of benzene-1,3-dicarbaldehyde and 3-azapentane-1,5-diaminein acetonitrile leads to isolation of an 18-membered imidazolidine-containing Schiff base macrocycle rather than the anticipated 24-membered tetraimine Schiff base macrocycle. This has occurred as a consequence of internal nucleophilic addition of the secondary amine functions across adjacent azomethine bonds. The X-ray crystal structure of the imidazolidine-containing Schiff base macrocycle is reported.
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S. M. Nelson:Pure Appl. Chem. 2461 (1980).
N. A. Bailey, M. M. Eddy, D. E. Fenton, G. Jones, S. Moss and A. Mukhopadhyay:J. Chem. Soc., Dalton Trans. 2281 (1984).
D. E. Fenton and R. Moody:J. Chem. Soc., Dalton Trans. 219 (1987).
P. Moore, N. W. Alcock, R. G. Kingston and C. G. Pierpoint:J. Chem. Soc., Dalton Trans. 1937 (1984).
D. H. Cook: Ph.D. Thesis (University of Sheffield), 1977.
A. E. Martell and R. Menif:J. Chem. Soc., Chem. Commun. 1521 (1989).
J. M. Lehn, J. Zagwinski, R. Meric, J. P. Vigneron, M. Cesario, J. Guilhem and C. Pascard:Tetrahedron Lett. 28, 3489 (1987).
N. A. Bailey, D. E. Fenton, R. J. Good, R. Moody and C. O. Rodriguez de Barbarin:J. Chem. Soc., Dalton Trans. 207 (1987).
S. M. Nelson, M. G. B. Drew and J. Nelson:J. Chem. Soc., Dalton Trans. 1679 (1981).
A. G. Kol'chinskii and K. B. Yatsimirskii:Teor. Eksp. Khim. 20, 92 (1984).
A preliminary report of the structure has been made; H. Adams, A. Atkinson, N. A. Bailey, D. E. Fenton, P. D. Hempstead, G. P. Westwood and R. Bastida: Abstracts, 23rd Reunion Bienal de la Real Sociedad Espanola de Quimica, Salamanca, 25-C-47 (1990).
G. M. Sheldrick,SHELXTL, An integrated system for solving, refining and displaying crystal structures from diffraction data (Revision 4), University of Gottingen, F.R. Germany, 1983.
G. P. Westwood: Ph.D. Thesis (University of Sheffield) 1990.
J. E. Baldwin:J. Chem. Soc., Chem. Commun. 734 (1976).
R. Menif, A. E. Martell, P. J. Squattrino and A. Clearfield:Inorg. Chem. 29, 4723 (1990).
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Adams, H., Bailey, N.A., Fenton, D.E. et al. Ring contraction in schiff base macrocycles: The X-Ray crystal structure of an imidazolidine-containing macrocycle. J Incl Phenom Macrocycl Chem 11, 63–69 (1991). https://doi.org/10.1007/BF01073685
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DOI: https://doi.org/10.1007/BF01073685