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Synthesis of Isomeric Dinitro and Diamino Derivatives of Polycyclic Crown Ethers: Dibenzo-18-crown-6 and Dibenzo-24-crown-8

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Abstract

Specific features of the synthesis of polycyclic crown ethers dibenzo-18-crown-6 and dibenzo-24-crown-8 and their dinitro and diamino derivatives have been studied. A mixture of isomers of dibenzocrown ether derivatives was obtained and separated. The spectral and thermal characteristics of the synthesized compounds and the kinetics of synthesis of dibenzo-24-crown-8 by the two-component condensation of pyrocatechol with 1-chloro-2-[2-(2-chloroethoxy)ethoxy]ethane in an alcoholic medium in the presence of a KOH template agent were studied.

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References

  1. Bezhin, N.A. and Dovhyi, I.I., Russ. Chem. Rev., 2015, vol. 84, no. 12, p. 1279. doi 10.1070/RCR4505

    Article  CAS  Google Scholar 

  2. Pethrick, R.A., Wilson, M.J., Affrossman, S., Holmes, D., and Lee, W.M., Polymer, 2000. vol. 41, p. 7111. doi 10.1016/S0032-3861(00)00043-4

    Google Scholar 

  3. Zaitova, G.A., Musaev, U.N., Tashmukhamedova, A.K., Khakimdzhanov, B.Sh., Saifullina, N.Zh., and Stempnevskaya, I.A., RF Patent no. 1784268, 1992.

    Google Scholar 

  4. Titova, Yu.A., Fedorova, O.V., Ovchinnikova, I.G., Maksimovskikh, A.I., Uimin, M.A., Rusinov, G.L., and Charushina, V.N., Macroheterocycles, 2014, vol. 7, no. 1, p. 23. doi 10.6060/mhc140481t

    Article  Google Scholar 

  5. Tunca, U. and Yagci, Y., Prog. Polym. Sci., 1994, vol. 19, no. 2, p. 233. doi 10.1016/0079-6700(94)90007-8

    Article  CAS  Google Scholar 

  6. Sakamoto, H., Kimura, K., and Shono, T., Eur. Polym. J., 1986, vol. 22, no. 2, p. 97. doi 10.1016/0014-3057(86) 90101-1

    Article  CAS  Google Scholar 

  7. Yang, L., Kang, Y., Wang, Y., Xu, L., Kita, H., and Okamoto, K., J. Membr. Sci., 2005, vol. 249, p. 33. doi 10.1016/j.memsci.2004.08.029

    Article  CAS  Google Scholar 

  8. Glushko, V.N., Tsirul’nikova, N.V., Blokhina, L.I., Pevtsova, L.A., Sadovskaya, N.Yu., Fetisova, T.S., and Podmareva, O.N., Naukoemk. Tekhnol., 2013, vol. 14, no. 3, p. 5.

    Google Scholar 

  9. Wang, D., Xing, J., Peng, J., and Wu, C., J. Chromatogr. A, 2003, vol. 1005, p. 1. doi 10.1016/S0021-9673(03)00884-7

    Article  CAS  PubMed  Google Scholar 

  10. Ludovica, R. and Fritz, V., ChemMedChem., 2014, vol. 8, no. 1, p. 3. doi 10.1007/3-540-12397-0_1

    Google Scholar 

  11. Feigenbaum, W.H. and Michel, R.H., J. Polym. Sci., 1971, vol. 9, no. 3, p. 817. doi 10.1002/pol.1971.150090322

    Article  CAS  Google Scholar 

  12. Smukste, I. and Smithrud, D.B., J. Org. Chem., 2003. vol. 68, p. 2547. doi 10.1021/jo026530q

    Google Scholar 

  13. Deetz, M.J., Shukla, R., and Smith, B.D., Tetrahedron, 2002, vol. 58, no. 4, p. 799. doi 10.1016/S0040-4020 (01)01108-5

    Article  CAS  Google Scholar 

  14. Saigo, K., Lin, R.-J., Kubo, M., Youda, A., and Hasegawa, M., Chem. Lett., 1986. vol. 15, no. 4, p. 519. doi 10.1246/cl.1986.519

    Google Scholar 

  15. Martyanov, T.P., Ushakov, E.N., Savelyev, V.A., and Klimenko, L.S., Russ. Chem. Bull., 2012. vol. 61, no. 12, p. 2282. doi 10.1007/s11172-012-0323-z

    Google Scholar 

  16. Rieckemann, B., Ebhardt, K.-B., and Umland, F., Z. Naturforsch. B, 1984, vol. 39, no. 4, p. 542.

    Article  Google Scholar 

  17. Parikh, V.B. and Menon, S.K., Mol. Cryst. Liq. Cryst., 2008, vol. 482, p. 71.

    Article  CAS  Google Scholar 

  18. Kalishevich, V.S., Timofeev, O.S., Zakharov, K.S., and Gren’, A.I., Russ. J. Org. Chem., 1988, vol. 24, no. 2, p. 349.

    Google Scholar 

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Correspondence to V. N. Glushko.

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Original Russian Text © V.N. Glushko, N.Yu. Sadovskaya, L.I. Blokhina, M.Yu. Zhila, S.K. Belus’, E.S. Vashchenkova, I.A. Shmeleva, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 8, pp. 1273–1279.

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Glushko, V.N., Sadovskaya, N.Y., Blokhina, L.I. et al. Synthesis of Isomeric Dinitro and Diamino Derivatives of Polycyclic Crown Ethers: Dibenzo-18-crown-6 and Dibenzo-24-crown-8. Russ J Gen Chem 88, 1595–1600 (2018). https://doi.org/10.1134/S1070363218080078

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  • DOI: https://doi.org/10.1134/S1070363218080078

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