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Synthesis and Properties of First Bis(fluoreno)crownophanes

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Abstract

Alkylation of 2,7-dihydroxy-9H-fluoren-9-one with 2-(2-chloroethoxy)ethanol, 2-[2-(2-chloroethoxy)-ethoxy]ethanol, and 2-{2-[2-(2-chloroethoxy)ethoxy]ethoxy}ethanol in dimethylformamide in the presence of potassium carbonate gave 78–80% of the corresponding diols which were treated with p-toluenesulfonyl chloride in a dioxanechloroform mixture in the presence of triethylamine at 0– 5°C (30 h). The resulting bis(p-toluene-sulfonates) were brought into condensation with 2,7-dihydroxy-9H-fluoren-9-one in a very dilute solution in dimethylformamide containing anhydrous potassium carbonate at 80–85°C. Appropriate treatment of the reaction mixture, followed by chromatographic purification afforded 53–27% of the first representatives of a new class of cyclophanes, bis(oxofluoreno)crownophanes. Raising the temperature to 95–105°C resulted in an appreciable decrease of the product yield. The yield of the target products did not increase on replacement of potassium carbonate by cesium carbonate.

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Authors and Affiliations

  1. Bogatskii Physicochemical Institute, National Academy of Sciences of Ukraine, Lyustdorfskaya doroga 86, Odessa, 65080, Ukraine

    A. Yu. Lyapunov, T. I. Kirichenko, E. Yu. Kulygina & N. G. Luk’yanenko

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  1. A. Yu. Lyapunov
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  2. T. I. Kirichenko
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  3. E. Yu. Kulygina
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  4. N. G. Luk’yanenko
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__________

Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 1, 2005, pp. 144–149.

Original Russian Text Copyright © 2005 by Lyapunov, Kirichenko, Kulygina, Luk’yanenko.

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Lyapunov, A.Y., Kirichenko, T.I., Kulygina, E.Y. et al. Synthesis and Properties of First Bis(fluoreno)crownophanes. Russ J Org Chem 41, 144–150 (2005). https://doi.org/10.1007/s11178-005-0138-6

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  • DOI: https://doi.org/10.1007/s11178-005-0138-6

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