Abstract
[6+4] Cycloaddition reactions of functionalized thiophene dioxides with various fulvenes provided the corresponding azulenes. The observed regiochemistry was explained in terms of the HOMO—LUMO orbital coefficients.
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K.-P, Zeller, in Houben-Weyl; Methoden der organischen Chemie, Georg Thieme, Stuttgart, 1985; Vol. V/2c, 127 pp.
T. Zieliñski, M. Kedziorek, and J. Jurczak, Tetrahedron Lett., 2005, 46, 6231; (b) M. Lamberto, C. Pagba, P. Piotrowiak, and E. Galoppini, Tetrahedron Lett., 2005, 46, 4895.
S. Ito, S. Kikuchi, N. Morita, and T. Asao, J. Org. Chem., 1999, 64, 5815.
T. Asao, S. Ito, and N. Morita, Tetrahedron Lett., 1988, 29, 2839; (b) D. A. Colby and T. D. Lash, J. Org. Chem., 2002, 67, 1031; (c) O. K. Abou-Zied, Spectrochim. Acta, Part A, 2005, 62, 245.
F. A. Andersen and D. R. Teufel, Int. J. Toxicol., 1999, 18, 27; (b) M. Guarrera, L. Turbino, and A. Rebora, J. Eur. Acad. Dermatol. Venerol., 2001, 15, 486.
K. Ziegler and K. Hafner, Angew. Chem., 1955, 67, 301; (b) L. T. Scott, M. A. Minton, and M. A. Kirms, J. Am. Chem. Soc., 1980, 102, 6311; (c) M. Yasunami, S. Miyoshi, N. Kanegae, and K. Takase, Bull. Chem. Soc. Jpn, 1993, 66, 892; (d) S. Carret, A. Blanc, Y. Coquerel, M. Berthod, A. E. Greene, and J.-P. Deprés, Angew. Chem., Int. Ed. (Engl.), 2005, 44, 5130.
V. G. Nenajdenko, A. E. Gavryushin, and E. S. Balenkova, Tetrahedron Lett., 2001, 42, 4397; (b) V. G. Nenajdenko, A. M. Moiseev, and E. S. Balenkova, Izv. Akad. Nauk, Ser. Khim., 2004, 2144 [Russ. Chem. Bull., Int. Ed., 2004, 53, 2241].
V. G. Nenajdenko, A. M. Moiseev, and E. S. Balenkova, Tetrahedron, 2005, 61, 10880; (b) V. G. Nenajdenko, A. M. Moiseev, and E. S. Balenkova, Izv. Akad. Nauk, Ser. Khim., 2005, 2117 [Russ. Chem. Bull., Int. Ed., 2005, 54, 2182]; (c) A. M. Moiseev, V. G. Nenajdenko, and E. S. Balenkova, Tetrahedron, 2006, 61, 4139.
S. E. Reiter, L. C. Dunn, and K. N. Houk, J. Am. Chem. Soc., 1977, 99, 4199; (b) D. Mukherjee, L. C. Dunn, and K. N. Houk, J. Am. Chem. Soc., 1979, 101, 251; (c) K. Kanematsu, H. Kazunobu, and D. Hirokazu, Heterocycles, 1981, 16, 1145; (d) Y. Lu, D. M. Lemal, and J. P. Jasinski, J. Am. Chem. Soc., 2000, 122, 2440; (e) J. Nakayama, Bull. Soc. Chem. Jpn, 2000, 73, 1; (f) Y. Lou, J. Chang, J. Jorgensen, and D. M. Lemal, J. Am. Chem. Soc., 2002, 124, 15302.
K. Hafner, K. H. Vöpel, G. Ploss, and C. König, Organic Syntheses, John Wiley & Sons, New York, 1973, Coll. Vol. 5, p. 431; (b) P. Rademacher, R. Stolevik, and W. Lüttke, Angew. Chem., Int. Ed. (Engl.), 1968, 10, 806; (c) N. F. Bondar’, E. V. Koroleva, T. N. Omel’chenko, and A. A. Akhrem, Zh. Org. Khim., 1981, 17, 2333 [J. Org. Chem. USSR, 1981, 17, 2084]; (d) I. Gupta and P. Yates, Synth. Commun., 1982, 13, 1007; (e) G. Nzabamwita, B. Kolani, and B. Jousseaume, Tetrahedron Lett., 1989, 30, 2207.
K. N. Houk, J. K. George, and R. E. Duke, Tetrahedron, 1974, 30, 523; (b) K. N. Houk, J. Sims, C. R. Watts, and L. J. Luskus, J. Am. Chem. Soc., 1973, 95, 7301.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 137–142, January, 2006.
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Moiseev, A.M., Balenkova, E.S. & Nenajdenko, V.G. [6+4] Cycloaddition reactions of acceptor thiophene dioxides: The synthesis of substituted azulenes. Russ Chem Bull 55, 141–146 (2006). https://doi.org/10.1007/s11172-006-0227-x
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DOI: https://doi.org/10.1007/s11172-006-0227-x