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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Ono, N., The Nitro Group in Organic Synthesis. Organic Nitro Chem. Ser., New York: VCH, 2001.
Perekalin, V.V., Lipina, E.S., Berestovitskaya, V.M., and Efremov, D.A., Nitroalkenes (Conjugated Nitro Compounds), London: J. Wiley, 1994, 256 p.
Kazuoki, N., Kamoshita, M., Takayuki, D., Yamada, H., and Takahashi, T., Tetrahedron Lett., 2001, vol. 42, no. 44, p. 7855.
Pogny, S., Nouri, S., Chiaroni, A., Guyot, M., and Samadi, N., J. Org. Chem., 2001, vol. 66, no. 22, p. 7263.
Satiago, C., Donald, C., Lane, C., Mac Kenzie, Roderich, A., and Wood, F., Chem. Commun., 2000, no. 18, p. 1767.
Jawamatsi, S., Matsubara, K., and Nagashima, H., J. Org. Chem., 1999, vol. 64, no. 26, p. 9625.
Arce, E., Carreno, M.C., Cid, M.B., and Ruano, J.L., J. Org. Chem., 1994, vol. 59, no 12, p. 3421.
Node, M., Imazato, H., Kurosaki, R., Kawano, Y., Inoue, T., Nishide, K., and Fuji, K., Heterocycles, 1996, vol. 42, no. 2, p. 811.
Chandler, M., Conroy, R., Cooper, A., and Lamont, R., J. Chem. Soc., Perkin Trans. 1, 1995, no. 9, p. 1189.
Cere, V., Montovani, G., Peri, F., Pollicino, S., and Ricci, A.A., Tetrahedron, 2000, vol. 56, no. 9, p. 1225.
Burkett, H. and Wright, W., J. Org. Chem., 1960, vol. 25, no. 2, p. 276.
Ono, N., Kamimura, A., and Kaji, A., J. Org. Chem., 1988, vol. 53, no. 2, p. 251.
Albertini, E., Barco, S., and Benneti, S., Tetrahedron Lett., 1994, vol. 35, no. 49, p. 929.
Habermann, J., Ley, S., and Scon, J., J. Chem. Soc., Perkin Trans. 1, 1999, no. 10, p. 1253.
Barltrop, B.J. and Nicholson, J.S., J. Chem. Soc., 1951, p. 2524.
Dudinskaya, A.A., Shvekhgeimer, G.A., Novikov, S.S., and Slovetskii, V.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1961, no. 3, p. 524.
Kataev, E.F. and Matveeva, P.S., Zh. Obshch. Khim.,1953, vol. 23, no. 3, p. 405.
Shin, C., Jamaura, M., Nui, E., Ishida, Y., Inui, E., and Yochimura, J., Bull. Chem. Soc. Japan, 1978, vol. 51, no. 9, p. 2618.
Barco, A., Benetti, S., Pollini, G., Spalluto, G., and Zanizato, V., Tetrahedron Lett., 1991, vol. 32, no. 22, p. 2517.
Anisimova, N.A., Berkova, G.A., Ladygin, V.V., and Berestovitskaya, V.M., Zh. Org. Khim., 2006, vol. 42, no. 8, p.1263.
Anisimova, N.A., Berestovitskaya, V.M., Berkova, G.A., and Ladygin, V.V., Zh. Org. Khim., 2006, vol. 42, no. 11, p. 1747.
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.
Wildman, W.C., Wildman, R.B., Norton, W.T., and Fine, J.B., J. Am. Chem. Soc., 1953, vol. 75, no. 7, p. 1912.
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.
Itoh, K., Ishida, H., and Chikaschita, H., Chem. Lett., 1982, no. 7, p. 1117.
Ono, N., Miyake, H., Kamimura, A., and Kaji, A., J. Chem. Soc., Perkin Trans. 1, 1987, no. 9, p. 1929.
Ionin, B.I., Ershov, B.A., and Kol’tsov, A.I., YaMR spektroskopiya v organcheskoi khimii (NMR Spectroscopy in Organic Chemistry), Liningrad: Khimiya, 1983.
Ionin, B.I. and Timofeeva, T.N., Usp. Khim., 1972, vol. 41, no. 4, p. 758.
Brandt, J. and Eglinton, G., Primeneniye spektroskopii v organicheskoi khimii (Applications of Spectroscopy in Organic Chemistry), Moscow: Mir, 1967, p. 277.
Masesane, I. and Steel, P.G., Tetrahedron Lett., 2004, vol. 45, p. 5007.
Porter, E., Wang, X., Lee, H., Weisblum, B., and Gellman, S.H., Nature, 2000, vol. 404, p. 565.
Appella, D.H., Barchi, I., Durell, S., and Gellman, S.H., J. Am. Chem. Soc., 1999, vol. 121, no. 10, p. 2309.
Shechter, H. and Conrad, F., J. Am. Chem. Soc., 1953, vol. 75, no. 22, p. 5610.
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.
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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