Abstract
The presented azoxy compound is an example of a new crown ether analogue. It has been synthesized by the reduction of an open chain dinitro compound with stannite under strongly alkaline conditions. A method for the separation of the azo and azoxy compounds formed simultaneously has been proposed. The structures of two crystallographically independent molecules of compound2 have been determined. In spite of the small size of the macroring in compound2, the phenyl residues around the azoxy group have atrans orientation.
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References
F. Vögtle:Supramolecular Chemistry — An Introduction, J. Wiley & Sons, Chichester-New York-Brisbane-Toronto-Singapore, 1991.
A. Merz and A. Karl:XVII International Symposium on Macrocyclic Chemistry, Provo, Utah, USA, August 1992, p. 64.
J. Bar and S. Bernstein:Acta Crystallogr. B37, 1569 (1981).
A. Dietrich, I.C. Paul, and D.Y. Curtin:J. Am. Chem. Soc. 96, 6372 (1974); O.S. Filipenko, V.I. Ponomarev, and L.O. Atovmyan:Doklady A. N. SSSR 242, 99 (1978); C.A.89, 207570.
J.F. Biernat, E. Luboch and A. Cygan:J. Coord. Chem. 27, 215 (1992).
J.F. Biernat, E. Jereczek, and A. Bujewski:Pol. J. Chem. 53, 2351 (1979).
J.F. Biernat, E. Luboch, A. Cygan, Yu.A. Simonov, A.A. Dvorkin, E. Muszalska, and R. Bilewixz:Tetrahedron 48, 4399 (1992).
G.M. Sheldrick: SHELX, a system of computer programs for X-ray structure determination, University of Cambridge, England (1976).
A.H. Cook and D.G. Jones:J. Chem. Soc. 1309 (1939).
J.F. Biernat and T. Wilczewski:Pol. J. Chem. 53, 513 (1979).
J. Kostrowicki, E. Luboch, B. Makuch, A. Cygan, A. Horbaczewski, and J.F. Biernat:J. Chromatogr. 454, 340 (1988).
S. Aoki, M. Shiga, M. Tazaki, H. Nakamura, M. Takagi, and K. Ueno:Chem. Lett. 1583 (1981).
J.F. Biernat, E. Luboch, A. Cygan, Yu.A. Simonov, and A.A. Dvorkin:XVII International Symposium on Macrocyclic Chemistry, Provo, Utah, USA, August 1992, p. 11.
A. Reissert:Ber 42, 1364 (1909); E. Müller and W. Kreutzmann:Ann. 495, 132 (1932).
G.M. Badger, R.G. Buttery, and G.E. Lewis:J. Chem. Soc., 2143 (1953).
C.J. Brown:Acta Crystallogr 21, 146 (1966); H. Hope and D. Victor:Acta Crystallogr. B25, 1849 (1969).
J. Dale:Acta Chem. Scand.27, 1115 (1973).
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Supplementary Data relating to this article have been deposited with the British Library as Supplementary Publication No. 82157 (11 pages).
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Biernat, J.F., Cygan, A., Luboch, E. et al. A 13-membered crown ether with an azoxy subunit in the macrocycle: Synthesis and X-ray structure. J Incl Phenom Macrocycl Chem 16, 209–218 (1993). https://doi.org/10.1007/BF00708791
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DOI: https://doi.org/10.1007/BF00708791