Abstract
A series of new calix[4]phenols, calix[4]resorcinols and calix[4]pyrogallols with acetylhydrazide substitutes has been␣synthesized with high yields by hydrazinolysis of ester group containing calix[4]arenes. The synthesized calix[4]phenols adopt the cone conformation while the calix[4]resorcinol and calix[4]pyrogallol derivatives prefer the boat conformation. The amide fragment of the hydrazide groups predominantly exists in the trans-conformation. The binding ability of synthesized calix[4]arenes toward transition and alkali metals by solvent extraction has been investigated.
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C.D. Gutsche: Calixarenes Revisited. In: J.F. Stoddart (ed.), Monograph in Supramolecular Chemistry, The Royal Society of Chemistry, Cambridge (1998)
Z. Asfary, V. Böhmer, J. Harrowfield, and J. Vicens (eds.) Calixarenes 2001, Kluwer Academic Publishers, Dordrecht (2001)
Machkhoshvili R.I., Shchelokov R.N. (2000) Russ. J. Coord. Chem 26: 677
V. Kogan, V. Zelentsov, G. Larin, and V. Lhukov: Complexes of transitional metals with hydrazones. In: A.Y. Tsivadze (ed.), Nauka, Moscow, (1990)
Stott K., Stonehouse J., Keeler J., Hwang T.L., Shaka A.J. (1995) J. Am. Chem. Soc. 117: 4199
HyperChem 7.03 Molecular Mechanics and Quantum Chemical Calculations Package, HyperCub Inc., Canada (2002)
Iwamoto K., Shinkai S. (1992) J. Org. Chem. 57: 7066
Iki N., Narumi F., Fujimoto T., Miyano S. (1998) J. Chem. Soc. Perkin Trans. 2: 2745
Iwanek W. (1998) Tetrahedron Asymmetry 9: 3171
A.N. Koppehele, Ph.D. Thesis, Dresden University of Technology, (2005)
Yamada A., Murase T., Kikukawa K., Arimura T., Shinkai S. (1991) J. Chem. Soc. Perkin Trans. 2 5: 793
Archer A.W., Claret P.A. (1970) J. Chem. Soc. Sect. C. kjkj: 1296
Giacosa A. (1879) J. Praktisch. Chemie. 2: 396
Davletshina G.R., Stibor I., Kazakova E.Kh., Pinkhasik E.M., Karataeva F.Kh., Konovalov A.I. (1997) Russ. J. Gen. Chem. 67: 1909
Alekseeva E.A., Bacherikov V.A., Gren A.I., Mazepa A.V., Gorbatyuk V.Y., Krasnoshchekaya S.P. (2000) Russ. J. Org. Chem 36: 1321
A.P. Grekov and V.Ya. Veselov: Physical chemistry of hydrazine. In: U.L. Spirin (ed.), Naukova Dumka, Kiev (1979)
Bellamy L.J. (1958) The IR Spectra of Complex Organic Molecules. 2nd edn. Wiley, New York, Methuen, London
Titov E., Grekov A., Rybachenkov I., Shevchenko V. (1968) Teor. Eksp. Khim. 4: 741
Hogberg A.G.S. (1980) J. Am. Chem. Soc. 102: 6046
Abis L., Dalcanale E., DuVosel A., Spera S. (1988) J. Org. Chem 53: 5475
Lhotak P., Stastny V., Zlatuskova P., Stibor I., Michlova V., Tradlecova M., Havlicek M., Sykora J. (2000) Collect. Czech. Chem. Commun. 65: 757
V.V. Syakaev, S.N. Podyachev, B.I. Buzykin, Sh.K. Latypov, W.D. Habicher, and A.I. Konovalov: J. Mol. Struct. (in press)
Burgess M.A. (1978) Metal Ions in Solution. Ellis Horwood, England
Acknowledgements
This work was supported by the Russian Fund for Basic Research (grants 04-03-32992a, 05-03-08086ofi_a, 05-03-32558a) and a grant of the Academy of Science of the Republic of Tatarstan (07-7.1-264).
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Podyachev, S.N., Syakaev, V.V., Sudakova, S.N. et al. Synthesis of New Calix[4]arenes Functionalizated by Acetylhydrazide Groups. J Incl Phenom Macrocycl Chem 58, 55–61 (2007). https://doi.org/10.1007/s10847-006-9117-y
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DOI: https://doi.org/10.1007/s10847-006-9117-y