PL EN


Preferencje help
Widoczny [Schowaj] Abstrakt
Liczba wyników
Tytuł artykułu

Lactones 17. Synthesis of Bicyclic Lactones with the Methyl- or gem-Dimethylcyclopropane System

Identyfikatory
Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
A new method of synthesis of bicyclic gamma-lactones with the methyl- or gem-dimethylcyclopropane system from gamma,delta unsaturated esters is described. The reaction of gamma-halo delta- lactones with DBU is the key step of this synthesis. The mechanism of the dehydrohalogenation- cyclization process of gamma-halo-delta-lactones is proposed. The structures of products were confirmed by both spectroscopic and crystallographic methods.
Rocznik
Strony
981--993
Opis fizyczny
Bibliogr. 30 poz., rys.
Twórcy
autor
  • Institute of Chemistry, Świętokrzyska Academy, Chęcińska 5, PL-25-020 Kielce, Poland
autor
  • Department of Chemistry, Agricultural University, Norwida 25, PL-50-375 Wrocław
  • Department of Chemistry, Agricultural University, Norwida 25, PL-50-375 Wrocław
  • Department of Chemistry, Agricultural University, Norwida 25, PL-50-375 Wrocław
  • Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, PL-50-383 Wrocław, Poland
autor
  • Faculty of Chemistry, University of Wrocław, F. Joliot-Curie 14, PL-50-383 Wrocław, Poland
Bibliografia
  • 1.Lactones 16: Wawrzenczyk C., Grabarczyk M., Biatonska A. and Ciunik Z., Tetrahedron, 59, ( (2003).
  • 2.Arlt D., Jautelat M. and Lantzsch R., Angew. Chem., 93, 719 (1981).
  • 3.Mann J. and Thomas A., Tetrahedron Lett., 27, 3533 (1986).
  • 4.Franck-Neumann M., Sedrati M., Vigneron J.P. and Bloy V., Angew. Chem., 97, 995 (1985).
  • 5.Mukaiyama T., Yamashita H. and Asami M., Chem. Letters, 385 (1983).
  • 6.Majewski M. and Snieckus V., J. Org. Chem., 49, 2682 (1984).
  • 7.Mann J. and Weymouth-Wilson A., Carbohydr. Res., 216, 511 (1991).
  • 8.Takano S., Kurotaki A., Takahashi M. and Ogasawara K., J. Chem. Soc., Perkin Trans. I, 91 (19:
  • 9.Bakksi D., Mahindroo V. K., Soman R. and Dev S., Tetrahedron, 45, 767 (1989).
  • 10.Lochyński S., Jarosz B., Walkowicz M. and Piqtkowski K., J. Prakt. Chem., 330, 284 (1988).
  • 11.Lebel H., Marcoux J.F., Molinaro C. and Charette A.B., Chem. Rev., 103, 977 (2003).
  • 12.Doyle M.P., Pieters R.J., Martin S.F., Austin R.E., Oalmann C.J. and Muller P., J. Am. Chem. Soc., 1423 (1991).
  • 13.Doyle M.P., Austin R.E., Bailey A.S., Dwyer M.P., Dyatkin A.B., Kalinin A.V., Kwan M.M.Y., Lira Oalmann C.J., Pieters R.J., Protopopova M.N., Raab C.E., Roos G.H.P., Zhou Q-L and Martin S.l J. Am. Chem. Soc., 117, 5763 (1995).
  • 14.Doyle M.P., Peterson C.S., Zhon Q-L and Nishiyama H., Chem. Commun., 211 (1997).
  • 15.Koskinen A.M.P. and Munoz L., J. Org. Chem., 58, 879 (1993).
  • 16.Moore J.D., Sprott K.T., Wr6blewski A.D. and Hanson P.R., Org. Lett., 4, 2357 (2002).
  • 17.Sabbioni G. and Jones J.B., J. Org. Chem., 52, 4565 (1987).
  • 18.Walser P., Rcnold P.,N’Goka V., Hosseinzadeh F. and Tamm C., Ilelv. Chim. Acta, 74, 1941(1991).
  • 19.Pirrung M.C., Dunlap S.E. and Trinks U.P., Helv. Chim. Acta, 72, 1301 (1989).
  • 20.Kelkar S.V., Arbale A.A., Joshi G.S. and Kulkami G.H., Synth. Commun., 20, 839 (1990).
  • 21.Ficini J. and d Angelo J., Tetrahedron Lett., 28, 2441 (1976).
  • 22.Obara R. and Wawrzenczyk C., J. Cosmet. Sci., 49, 299 (1988).
  • 23.Obara R., Olejniczak T. and Wawrzenczyk C., J. Soc. Cosmet. Chem., 46, 321 (1995).
  • 24.Johnson W.S., Wcrthemann L., Barlett W.R.R., Broksom T.J., Li T.T., Faulkner D.J. and Peterson M.R., J. Am. Chem. Soc., 92, 741 (1970).
  • 25.Obara R. and Wawrzenczyk C., Polish Pat. Appl., 2003, No P-360889.
  • 26.Mori K. and Nakazono Y., Tetrahedron, 42, 283 (1986).
  • 27.Snider B.B. and Johnston M.I., Tetrahedron Lett., 26, 5497 (1985).
  • 28.Sheldrick G.M., Acta Crystallorg., A46, 467 (1990).
  • 29.Sheldrick G.M., SHELXL97-. Program for the Refinement of Crystal Structures; University of Gottingen: Germany, 1997
  • 30.Serres C. and Fields E.K., J. Am. Chem. Soc., 82, 4681 (1960).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ3-0002-0108
JavaScript jest wyłączony w Twojej przeglądarce internetowej. Włącz go, a następnie odśwież stronę, aby móc w pełni z niej korzystać.