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Synthesis and structure of nitrocyclohexenylcarboxylates

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Abstract

The diene condensation of 3-nitro- and 3-bromo-3-nitroacrylates with 2,3-dimethyl-1,3-butadiene and isoprene obtained under the reaction condition from 3-methyl-3-thiolene-1,1-dioxide was investigated. The formed 6-nitro-3-cyclohexenylcarboxylates were subjected to the intramolecular transformation (dehydration and dehydrohalogenation) to give the corresponding nitrocyclohexadienyl- and arylcarboxylates. The structure of the obtained compounds was established from the IR, 1H NMR spectra and independent synthesis.

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References

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

    Book  Google Scholar 

  2. Perekalin, V.V., Lipina, E.S., Berestovitskaya, V.M., and Efremov, D.A., Nitroalkenes (Conjugated Nitro Compounds), London: J. Wiley, 1994, 256 p.

    Google Scholar 

  3. Kazuoki, N., Kamoshita, M., Takayuki, D., Yamada, H., and Takahashi, T., Tetrahedron Lett., 2001, vol. 42, no. 44, p. 7855.

    Article  Google Scholar 

  4. Pogny, S., Nouri, S., Chiaroni, A., Guyot, M., and Samadi, N., J. Org. Chem., 2001, vol. 66, no. 22, p. 7263.

    Article  Google Scholar 

  5. Satiago, C., Donald, C., Lane, C., Mac Kenzie, Roderich, A., and Wood, F., Chem. Commun., 2000, no. 18, p. 1767.

  6. Jawamatsi, S., Matsubara, K., and Nagashima, H., J. Org. Chem., 1999, vol. 64, no. 26, p. 9625.

    Article  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.

    Article  CAS  Google Scholar 

  8. Node, M., Imazato, H., Kurosaki, R., Kawano, Y., Inoue, T., Nishide, K., and Fuji, K., Heterocycles, 1996, vol. 42, no. 2, p. 811.

    Article  CAS  Google Scholar 

  9. Chandler, M., Conroy, R., Cooper, A., and Lamont, R., J. Chem. Soc., Perkin Trans. 1, 1995, no. 9, p. 1189.

  10. Cere, V., Montovani, G., Peri, F., Pollicino, S., and Ricci, A.A., Tetrahedron, 2000, vol. 56, no. 9, p. 1225.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  13. Albertini, E., Barco, S., and Benneti, S., Tetrahedron Lett., 1994, vol. 35, no. 49, p. 929.

    Article  Google Scholar 

  14. Habermann, J., Ley, S., and Scon, J., J. Chem. Soc., Perkin Trans. 1, 1999, no. 10, p. 1253.

  15. Barltrop, B.J. and Nicholson, J.S., J. Chem. Soc., 1951, p. 2524.

  16. Dudinskaya, A.A., Shvekhgeimer, G.A., Novikov, S.S., and Slovetskii, V.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1961, no. 3, p. 524.

  17. Kataev, E.F. and Matveeva, P.S., Zh. Obshch. Khim.,1953, vol. 23, no. 3, p. 405.

    CAS  Google Scholar 

  18. Shin, C., Jamaura, M., Nui, E., Ishida, Y., Inui, E., and Yochimura, J., Bull. Chem. Soc. Japan, 1978, vol. 51, no. 9, p. 2618.

    Article  CAS  Google Scholar 

  19. Barco, A., Benetti, S., Pollini, G., Spalluto, G., and Zanizato, V., Tetrahedron Lett., 1991, vol. 32, no. 22, p. 2517.

    Article  CAS  Google Scholar 

  20. Anisimova, N.A., Berkova, G.A., Ladygin, V.V., and Berestovitskaya, V.M., Zh. Org. Khim., 2006, vol. 42, no. 8, p.1263.

    Google Scholar 

  21. Anisimova, N.A., Berestovitskaya, V.M., Berkova, G.A., and Ladygin, V.V., Zh. Org. Khim., 2006, vol. 42, no. 11, p. 1747.

    Google Scholar 

  22. Anisimova, N.A., Berestovitskaya, V.M., Bagryanskaya, I.Yu., Ivanova, M.E., and Kuzhaeva, A.A., Zh. Obshch. Khim., 2010, vol. 80, no. 2, p. 283.

    Google Scholar 

  23. Wildman, W.C., Wildman, R.B., Norton, W.T., and Fine, J.B., J. Am. Chem. Soc., 1953, vol. 75, no. 7, p. 1912.

    Article  CAS  Google Scholar 

  24. Berestovitskaya, V.M., Anisimova, N.A., Kuzhaeva, A.A., Berkova, G.A., and Deiko, L.I., Zh. Obshch. Khim., 2007, vol. 77, no. 1, p. 29.

    Google Scholar 

  25. Itoh, K., Ishida, H., and Chikaschita, H., Chem. Lett., 1982, no. 7, p. 1117.

  26. Ono, N., Miyake, H., Kamimura, A., and Kaji, A., J. Chem. Soc., Perkin Trans. 1, 1987, no. 9, p. 1929.

  27. Ionin, B.I., Ershov, B.A., and Kol’tsov, A.I., YaMR spektroskopiya v organcheskoi khimii (NMR Spectroscopy in Organic Chemistry), Liningrad: Khimiya, 1983.

    Google Scholar 

  28. Ionin, B.I. and Timofeeva, T.N., Usp. Khim., 1972, vol. 41, no. 4, p. 758.

    CAS  Google Scholar 

  29. Brandt, J. and Eglinton, G., Primeneniye spektroskopii v organicheskoi khimii (Applications of Spectroscopy in Organic Chemistry), Moscow: Mir, 1967, p. 277.

    Google Scholar 

  30. Masesane, I. and Steel, P.G., Tetrahedron Lett., 2004, vol. 45, p. 5007.

    Article  CAS  Google Scholar 

  31. Porter, E., Wang, X., Lee, H., Weisblum, B., and Gellman, S.H., Nature, 2000, vol. 404, p. 565.

    Article  CAS  Google Scholar 

  32. Appella, D.H., Barchi, I., Durell, S., and Gellman, S.H., J. Am. Chem. Soc., 1999, vol. 121, no. 10, p. 2309.

    Article  CAS  Google Scholar 

  33. Shechter, H. and Conrad, F., J. Am. Chem. Soc., 1953, vol. 75, no. 22, p. 5610.

    Article  CAS  Google Scholar 

  34. Sarkisyan, Z.M., Sadikov, K.D., Smirnov, A.S., Kuzhaeva, A.A., Anisimova, N.A., Deiko, L.I., and Berestovitskaya, V.M., Zh. Org. Khim., 2004, vol. 40, no. 6, p. 944.

    Google Scholar 

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Correspondence to N. A. Anisimova.

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Original Russian Text © N.A. Anisimova, A.A. Kuzhaeva, G.A. Berkova, V.M. Berestovitskaya, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 9, pp. 1507–1514.

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Anisimova, N.A., Kuzhaeva, A.A., Berkova, G.A. et al. Synthesis and structure of nitrocyclohexenylcarboxylates. Russ J Gen Chem 81, 1845–1852 (2011). https://doi.org/10.1134/S1070363211090180

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  • DOI: https://doi.org/10.1134/S1070363211090180

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