Skip to main content
SpringerLink
Log in

Synthesis and Structure of Cyclohexenes Functionalized by Nitro and Trifluoro(chloro)methyl Groups

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

Abstract

Cyclohexenes functionalized by nitro and trihalomethyl groups were produced by condensation of 1-nitro- and 1-bromo-1-nitro-3,3,3-trifluoro(chloro)propenes with 2-methyl- and 2,3-dimethyl-1,3-butadienes; their structure was characterized by IR, 1H, 13C, 19F NMR spectroscopy, and X-ray diffraction method.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Ono, N., The Nitro Group in Organic Synthesis, Organic Nitro Chem. Ser., New York: VCH, 2001, p. 372.

    Book  Google Scholar 

  2. Perekalin, V.V., Lipina, E.S., Berestovitskaya, V.M., and Efremov, D.A., Nitroalkenes. Conjugated Nitro Compounds, Chichester: John Wiley and Sons, 1994.

    Google Scholar 

  3. Nakai, K., Kamoshita, M., Doi, T., Yamada, H., and Takahashi, T., Tetrahedron Lett., 2001, vol. 42, no. 44, p. 7855. doi 10.1016/S0040-4039(01)01655-0

    Article  CAS  Google Scholar 

  4. Poigny, S., Nouri, S., Chiaroni, A., Guyot, M., and Samadi, M., J. Org. Chem., 2001, vol. 66, no. 22, p. 7263. doi 10.1021/jo010154c

    Article  CAS  PubMed  Google Scholar 

  5. Carballares, S., Craig, D., Lane, C.A.L., MacKenzie, A.R., Mitchell, W.P., and Wood, A., Chem. Commun., 2000, no. 18, p. 1767. doi 10.1039/B005533F

    Article  Google Scholar 

  6. Jwamatsu, S., Matsubara, K., and Nagashima, H., J. Org. Chem., 1999, vol. 64, no. 26, p. 9625. doi 10.1021/jo9912146

    Article  CAS  Google Scholar 

  7. Arce, E., Carreno, M.C., Cid, M.B., and Ruano, J.L., J. Org. Chem., 1994, vol. 59, no. 12, p. 3421. doi 10.1021/jo00091a035

    Article  CAS  Google Scholar 

  8. Node, M., Jmazato, H., Kurosaki, R., Kawano, Y., Inoue, T., Nishide, K., and Fuji, K., Heterocycles, 1996, vol. 42, no. 2, p. 811. doi 10.3987/COM-95-S88

    Article  CAS  Google Scholar 

  9. Chandler, M., Conroy, R., Cooper, A.W.J., Lamont, R.B., Scicinski, J.J., Smart, J.E., Storer, R., Weir, N.G., Wilson, R.D., and Wyatt P.G., J. Chem. Soc., Per. Trans. 1, 1995, no. 9, p. 1189. doi 10.1039/P19950001189

    Article  Google Scholar 

  10. Cere, V., Montovani, G., Peri, F., Pollicino, S., and Ricci, A., Tetrahedron, 2000, vol. 56, no. 9, p. 1225. doi 10.1016/S0040-4020(00)00011-9

    Article  CAS  Google Scholar 

  11. Burkett, H. and Wright, W., J. Org. Chem., 1960, vol. 25, no. 2, p. 276. doi 10.1021/jo01072a614

    Article  CAS  Google Scholar 

  12. Ono, N., Kamimura, A., and Kaji, A., J. Org. Chem., 1988, vol. 53, no. 2, p. 251. doi 10.1021/jo00237a005

    Article  CAS  Google Scholar 

  13. Albertini, E., Barco, S., Benetti, S., De Risi, C., Pollini, G.P., Romagnoli, R., and Zanirato, V., Tetrahedron Lett., 1994, vol. 35, no. 49, p. 9297. doi 10.1016/0040-4039 (94)88492-7

    Article  CAS  Google Scholar 

  14. Habermann, J., Ley, S.V., and Scott, J.S., J. Chem. Soc., Per. Trans. 1, 1999, no. 10, p. 1253. doi 10.1039/A901802F

    Article  Google Scholar 

  15. Barltrop, J.A. and Nicholson, J.S., J. Chem. Soc., 1951, p. 2524. doi 10.1039/JR9510002524

    Google Scholar 

  16. Dudinskaya, A.A., Shvekhgeimer, G.A., and Novikov, S.S., Russ. Chem. Bull., 1961, vol. 10, no. 3, p. 484. doi 10.1007/BF01131073

    Article  Google Scholar 

  17. Dudinskaya, A.A., Shvekhgeimer, G.A., and Novikov, S.S., Russ. Chem. Bull., 1961, vol. 10, no. 3, p. 482. doi 10.1007/BF01131072

    Article  Google Scholar 

  18. Dudinskaya, A.A., Novikov, S.S., and Shvekhgeimer, G.A., Russ. Chem. Bull., 1965, vol. 14, no. 11, p. 1988. doi 10.1007/BF00845896

    Article  Google Scholar 

  19. Kuzhaeva, A.A., Berestovitskaya, V.M., Deiko, L.I., Anisimova, N.A., and Berkova G.A., Russ. J. Gen. Chem., 2002, vol. 72, no. 10, p. 1652. doi 10.1023/A:1023360322616

    Article  CAS  Google Scholar 

  20. Berestovitskaya, V.M., Anisimova, N.A., Kuzhaeva, A.A., Berkova, G.A., Deiko, L.I., Russ. J. Gen. Chem., 2007, vol. 77, no. 1, p. 25. doi 10.1134/S1070363207010045

    Article  CAS  Google Scholar 

  21. Prech, E., Byul’mann, F., and Affol’ter, K., Opredelenie stroeniya organicheskikh soedinenii (Structure Determination of Organic Compounds), Moscow: BINOM. Laboratoriya Znanii, 2013.

    Google Scholar 

  22. Rowland, R.S. and Taylor, R., J. Phys. Chem., 1996, vol. 100, no. 18, p. 7384. doi 10.1021/jp953141+

    Article  CAS  Google Scholar 

  23. Gordon, A.J. and Ford, R.A., The Chemist’s Companion. A Handbook of Practical Data, Techniques and References, New York: Wiley, 1972.

    Google Scholar 

  24. Allen, F.H., Acta Crystallogr. (B), 2002, vol. 58, p. 380. doi 10.1107/S0108768102003890

    Article  CAS  Google Scholar 

  25. Bruno, I.J., Cole, J.C., Edgington, P.R., Kessler, M., Macrae, C.F., McCabe, P., Pearson, J., and Taylor, R., Acta Crystallogr. (B), 2002, vol. 58, p. 389. doi 10.1107/S0108768102003324

    Article  CAS  Google Scholar 

  26. Compton, M., Higgins, H., MacBeth, L., Osborn, J., and Burkett, H., J. Am. Chem. Soc., 1949, vol. 71, no. 9, p. 3229. doi 10.1021/ja01177a085

    Article  CAS  Google Scholar 

  27. Lee, S.A., US Patent 5248832, 1993, Russian Patent 2056402, Byull. Izobret., 1996, no. 8.

    Google Scholar 

  28. Brower, F. and Burkett, H., J. Am. Chem. Soc., 1953, vol. 75, no. 5, p. 1082. doi 10.1021/ja01101a021

    Article  CAS  Google Scholar 

  29. Shechter, H., Ley, D.E., and Roberson, E.B., J. Am. Chem. Soc., 1956, vol. 78, no. 19, p. 4984. doi 10.1021/ja01600a049

    Article  Google Scholar 

  30. Durden, J.A., Heywood, D.L., Sousa, A.A., and Spurr, H.W., J. Agr. Food Chem., 1970, vol. 18, no. 1, p. 50. doi 10.1021/jf60167a011

    Article  CAS  Google Scholar 

  31. Dornow, A. and Muller, A., Chem. Ber., 1960, vol. 93, no. 1, p. 32. doi 10.1002/cber.19600930108

    Article  CAS  Google Scholar 

  32. Anisimova, N.A., Slobodchikova, E.K., Kuzhaeva, A.A., Stukan’, E.V., Bagryanskaya, I.Yu., and Berestovitskaya, V.M., Russ. J. Org. Chem., 2016, vol. 52, no. 10, p. 1379. doi 10.1134/S1070428016100018

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Herzen State Pedagogical University of Russia, nab. reki Moiki 48, St. Petersburg, 191186, Russia

    N. A. Anisimova, E. K. Slobodchikova, V. M. Berestovitskaya & A. A. Kuzhaeva

  2. St. Petersburg State University of Industrial Technologies and Design, St. Petersburg, Russia

    N. A. Anisimova

  3. Altai State Agricultural University, Barnaul, Russia

    M. E. Ivanova

  4. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia

    T. V. Rybalova

  5. Novosibirsk State University, Novosibirsk, Russia

    T. V. Rybalova

Authors
  1. N. A. Anisimova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. K. Slobodchikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. M. Berestovitskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. E. Ivanova
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. A. Kuzhaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. T. V. Rybalova
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to N. A. Anisimova.

Additional information

Original Russian Text © N.A. Anisimova, E.K. Slobodchikova, V.M. Berestovitskaya, M.E. Ivanova, A.A. Kuzhaeva, T.V. Rybalova, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 5, pp. 738–746.

Deceased.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Anisimova, N.A., Slobodchikova, E.K., Berestovitskaya, V.M. et al. Synthesis and Structure of Cyclohexenes Functionalized by Nitro and Trifluoro(chloro)methyl Groups. Russ J Gen Chem 88, 883–891 (2018). https://doi.org/10.1134/S1070363218050079

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218050079

Keywords

Search

Navigation