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Synthesis of monoazacrown ethers under phase-transfer catalysis

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Abstract

A procedure has been proposed for the synthesis of monoazacrown ethers by reaction of N-benzyldiethanolamine with oligo(ethylene glycol) bis-p-toluenesulfonates in a two-phase system aromatic hydrocarbon-50% aqueous alkali, followed by removal of the benzyl group by catalytic hydrogenolysis. The maximal yields of N-benzylaza-12-crown-4, -18-crown-6, and -21-crown-7 were achieved by adding 4–10 equiv of LiCl, BaBr2, and CsCl, respectively, to the reaction mixture, which probably indicated template effect.

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Authors and Affiliations

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

    N. G. Luk’yanenko, S. S. Basok, E. Yu. Kulygina, T. Yu. Bogashchenko & I. S. Yakovenko

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  1. N. G. Luk’yanenko
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  2. S. S. Basok
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  3. E. Yu. Kulygina
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  4. T. Yu. Bogashchenko
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  5. I. S. Yakovenko
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Corresponding author

Correspondence to E. Yu. Kulygina.

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Original Russian Text © N.G. Luk’yanenko, S.S. Basok, E.Yu. Kulygina, T.Yu. Bogashchenko, I.S. Yakovenko, 2012, published in Zhurnal Organicheskoi Khimii, 2012, Vol. 48, No. 10, pp. 1350–1357.

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Luk’yanenko, N.G., Basok, S.S., Kulygina, E.Y. et al. Synthesis of monoazacrown ethers under phase-transfer catalysis. Russ J Org Chem 48, 1345–1352 (2012). https://doi.org/10.1134/S1070428012100156

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  • DOI: https://doi.org/10.1134/S1070428012100156

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