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Tytuł artykułu

Synthesis and Structure of Spirocyclic Tetrahydrothiophene Derivatives Bearing a 'Cage' Residue

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
Trapping of the thiocarbonyl S-methanide 4 with tetracyanoethene and N-methylmaleimide led to the [3+2]-cycloadducts 11 and 12, respectively. The structures of these cycloadducts were established by X-ray crystallography. The 1,3-dipole 4 has been generated by thermal decomposition of the corresponding 2,5-dihydro-1,3,4-thiadiazole 2, which was prepared by the 1,3-dipolar cycloaddition of diazomethane with thioketone 1.
Rocznik
Strony
973--979
Opis fizyczny
Bibliogr. 24 poz., rys.
Twórcy
autor
  • Section of Heteroorganic Compounds, University of Łódź, Narutowicza 68, PL-90-136 Łódź, Poland
autor
  • Section of Heteroorganic Compounds, University of Łódź, Narutowicza 68, PL-90-136 Łódź, Poland
autor
  • Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
  • Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland
Bibliografia
  • 1.Mloston G. and Heimgartner H., Polish J. Chem., 74, 1503 (2000).
  • 2.Mloston G. and Heimgartner H., in ‘The Chemistry of Heterocyclic Compounds, Vol. 59: Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products’, Eds. Padwa A. and Pearson W.H., J. Wiley & Sons, New York, 2002, p. 315.
  • 3.Huisgen R., Li X., Gicra H. and Langhals E.,Helv. Chim. Acta, 84, 981 (2001).
  • 4.Huisgen R., Mloston G., Polbom K. and Sustmann R., Chem. Eur. J., 9, 2256 (2003).
  • 5.Romariski J. and Mloston G., Synthesis, 1355 (2002).
  • 6.Read C.E., Martins F.J.C. and Viljoen A.M., Tetrahedron Lett., 45, 7655 (2004).
  • 7.Romariski J., Szynkicwicz S. and Mloston G., Synthesis, 2259 (2003).
  • 8.Huisgen R. and Mloston G., Polish J. Chem., 73, 635 (1999).
  • 9.Lerman B.M.,Galin F.Z.,UmanskayaL.A. and Tolstikov G.A., J.Org. Chem. USSR, 14,2336(1978).
  • 10.Dekker T.G. and Oliver D.W., S. Afr. J. Chem., 32, 45 (1979).
  • 11.Marchand A.P. and Kay a R.,J. Org. Chem., 48, 4392(1983).
  • 12.Mehta G. and Reddy M.S., Tetrahedron Lett., 31,2039 (1990).
  • 13.Johnson C.K., ‘ORTEPII’, Report ORNL-5138, Oak Ridge National Laboratory, Oak Ridge, Tennessee, 1976.
  • 14.Cookson R.C., Crundwell E. and Hudec J., Chem. Ind. (London), 1003 (1958).
  • 15.Eaton P.E., Cassar L., Hudson R.A. and Hwang D.R., J. Org. Chem.,4\, 1445 (1976).
  • 16.Martins F.J.C., Viljoen A.M., Kruger H.G., Fourie L., Roscher J., Joubert A.J. and Wcssels P.L., Tetrahedron, 57, 1601 (2001).
  • 17.Hooft R., KappaCCD Collect Software, Nonius BV, Delft, The Netherlands, 1999.
  • 18.Otwinowski Z. and Minor W., in ‘Methods in Enzymology’, Vol. 276, ‘Macromolecular Crystallography’, Part A, Eds. Carter C.W., Jr. and Sweet R.M., Academic Press, New York, 1997, p. 307.
  • 19.Blessing R.H., Acta Crystallogr., Sect. A, 51, 33 (1995).
  • 20.Altomare A., Cascarano G., Giacovazzo C., Guagliardi A., Burla M.C., Polidori G. and Camalli M., SIR92, J. Appl. Crystallogr., 27, 435 (1994).
  • 21.a) Maslen E.N.,Fox A.G. and O’Keefe M.A., in international Tables for Crystallography’, Ed. Wilson A.J.C., Kluwer Academic Publishers, Dordrecht, 1992, Vol. C, Table 6.1.1.1, p. 477; b) Creagh D.C. and McAuley W.J., ibid., Table 4.2.6.8, p. 219; c) Creagh D.C. and 1 lubbell J.H., ibid., Table4.2.4.3, p. 200.
  • 22.Stewart R.F., Davidson E.R. and Simpson W.T., J. Chem. Phys., 42, 3175 (1965).
  • 23.Ibers J.A. and Hamilton W.C., Acta Crystallogr., 17, 781 (1964).
  • 24.Sheldrick G.M., SHELXL97, Program for the Refinement of Crystal Structures, University of Gottingen, Germany, 1997.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ3-0002-0107
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