Skip to main content
Log in

Spirocyclic 2,5-dihydro-1H-imidazole 1-oxyl radicals with a mesogenic substituent on C4. Synthesis and crystal structure

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Stable spirocyclic 2,5-dihydro-1H-imidazole 1-oxyl radicals containing a mesogenic fragment were synthesized on the basis of 1-[4-hydroxy(alkoxy)phenyl]-2-hydroxyamino-2-methylpropan-1-ones. The crystalline structure of two aminoxyl radicals was determined by X-ray analysis.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Tamura, R., Uchida, Y., and Suzuki, K., Liquid Crystals beyond Display: Chemistry, Physics, and Applications, Li, Q., Ed., Hoboken: Wiley, 2012, p. 83; Tamura, R., Uchida, Y., and Suzuki, K., Nitroxides: Theory, Experiment, and Applications, Kokorin, A.I., Ed., Croatia: InTec, 2012, p. 191.

  2. Ikuma, N., Tamura, R., Shimono, S., Kawame, N., Tamada, O., Sakui, N., Yamauchi, J., and Yamamoto, Y., Angew. Chem., Int. Ed., 2004, vol. 43, p. 3677; Tamura, R., Uchida, Y., and Ikuma, N., J. Mater. Chem., 2008, vol. 18, p. 2872.

    Article  CAS  Google Scholar 

  3. Ikuma, N., Tamura, R., Masaki, K., Uchida, Y., Shimono, S., Yamauchi, J., Aoki, J., and Nohira, H., Ferroelectrics, 2006, vol. 343, p. 119; Ikuma, N., Uchida, Y., Tamura, R., Suzuki, K., Yamauchi, J., Aoki, Y., and Nohira, H., Mol. Cryst. Liq. Cryst., 2009, vol. 50, p. 108.

    Article  CAS  Google Scholar 

  4. Uchida, Y., Ikuma, N., Tamura, R., Shimono, S., Noda, Y., Yamauchi, J., Aoki, Y., and Nohira, H., J. Mater. Chem., 2008, vol. 18, p. 2950; Uchida, Y., Suzuki, K., Tamura, R., Ikuma, N., Shimono, S., Noda, Y., and Yamauchi, J., J. Am. Chem. Soc., 2010, vol. 132, p. 9746.

    Article  CAS  Google Scholar 

  5. Kogo, R., Araoka, F., Uchida, Y., Tamura, R., Ishikawa, K., and Takezoe, H., Appl. Phys. Express, 2010, vol. 3, no. 041701.

    Google Scholar 

  6. Hayashi, S., Saha, S., and Hamaguchi, H., IEEE Trans. Magn., 2006, vol. p. 42, 12.

    Article  CAS  Google Scholar 

  7. Schmidt, W., Vögtle, F., and Poetsch, E., Justus Liebigs Ann. Chem., 1995, p. 1319; Calaminus, W., Vögtle, F., and Eidenschink, R., Z. Naturforsch., Teil B, 1986, vol. 41, p. 1011; Boettcher, J., Hartmann, R., and Vögtle, F., Chem. Ber., 1992, vol. 125, p. 1865; Poetsch, E., Schmidt, W., Vögtle, F., and Feuerbacher, N., FRG Patent no. 19 755 245, 1999; Chem. Abstr., 1999, vol. 131, np. P 65 963 j; Feuerbacher, N., Vögtle, F., Windscheidt, J., Poetsch, E., and Nieger, M., Synthesis, 1999, p. 117.

    Google Scholar 

  8. Miyazawa, K., Yufit, D.S., Howard, J.A.K., and de Meijere, A., Eur. J. Org. Chem., 2000, p. 4109; Miyazawa, K., Demus, D., and de Meijere, A., Mol. Cryst. Liq. Cryst., 2001, vol. 364, p. 253.

    Google Scholar 

  9. Itoh, T., Kanbara, M., Nakajima, S., Sakuta, Y., Hayase, S., Kawatsura, M., Kato, T., Miyazawa, K., and Uno, H., J. Fluorine Chem., 2009, vol. 130, p. 1157.

    Article  CAS  Google Scholar 

  10. Okazaki, S., Mannan, M.A., Sawai, K., Masumizu, T., Miura, Y., and Takeshita, K., Free Radic. Res., 2007, vol. 41, p. 1069.

    Article  CAS  Google Scholar 

  11. Kirilyuk, I.A., Polienko, Y.F., Krumkacheva, O.A., Strizhakov, R.K., Gatilov, Y.V., Grigorèv, I.A., and Bagryanskaya, E.G., J. Org. Chem., 2012, vol. 77, p. 8016.

    Article  CAS  Google Scholar 

  12. Uchida, Y., Matsuoka, N., Takahashi, H., Shimono, S., Ikuma, N., and Tamura, R., Heterocycles, 2007, vol. 74, p. 607; Suzuki, K., Mazhukin, D.G., Takahashi, H., Uchida, Y., Tamura, R., and Grigor’ev, I.A., Heterocycles, 2009, vol. 78, p. 3091.

    Article  CAS  Google Scholar 

  13. Tamura, R., Suzuki, K., Uchida, Y., and Noda, Y., Electron Paramagnetic Resonance, Gilbert, B.C., Murphy, D.M., and Chechik, V., Eds., London: Roy. Soc. Chem., 2012, vol. 23, p. 1.

  14. Sevast’yanova, T.K. and Volodarskii, L.B., Izv. Akad. Nauk SSSR, Ser. Khim., 1972, p. 2339; Reznikov, V.A. and Volodarskii, L.B., Izv. Akad. Nauk, Ser. Khim., 1997, p. 1654.

    Google Scholar 

  15. Imidazoline Nitroxides: Synthesis and Properties, Volodarsky, L.B., Ed., Boca Raton: CRC, 1988, p. 1.

    Google Scholar 

  16. Boubekeur, K., Syssa-Magalé, J.-L., Palvadeau, P., and Schöllhorn, B., Tetrahedron Lett., 2006, vol. 47, p. 1249.

    Article  CAS  Google Scholar 

  17. Wigbers, C., Prigge, J., Zhongchen, M., Frohlich, R., Lifeng, Ch., and Wurthwein, E.-U., Eur. J. Org. Chem., 2011, p. 861.

    Google Scholar 

  18. Al-Eryani, W.F.A., Srinivasa, H.T., Jeyaseelan, S., Sadashivaiah, T., and Devarajegowda, H.C., Acta Crystallogr., Sect. E, 2011, vol. 67, p. 840.

    Article  Google Scholar 

  19. Volodarskii, L.B., Lapik, A.S., Russkikh, V.V., Kobrin, V.S., Lavretskaya, E.F., Volkova, L.I., Sarkisyan, D.A., and Borisov, M.M., USSR Inventor’s Certificate no. 657 016, 1979; Chem. Abstr., 1979, vol. 91, no. P 68 767 q.

  20. Vasconcelos, U., Dalmolin, E., and Merlo, A., Org. Lett., 2005, vol. 7, p. 1027.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. V. Zaytseva.

Additional information

Original Russian Text © E.V. Zaytseva, Yu.V. Gatilov, S.A. Amitina, R.Tamura, I.A. Grigor’ev, D.G. Mazhukin, 2014, published in Zhurnal Organicheskoi Khimii, 2014, Vol. 50, No. 1, pp. 78–83.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zaytseva, E.V., Gatilov, Y.V., Amitina, S.A. et al. Spirocyclic 2,5-dihydro-1H-imidazole 1-oxyl radicals with a mesogenic substituent on C4. Synthesis and crystal structure. Russ J Org Chem 50, 72–77 (2014). https://doi.org/10.1134/S107042801401014X

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S107042801401014X

Keywords

Navigation