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Russian Journal of Organic Chemistry

, Volume 43, Issue 1, pp 40–49 | Cite as

Reaction of vinylidenecyclopropanes with aromatic imines in the presence of Lewis acids

  • A. V. Stepakov
  • A. G. Larina
  • A. P. Molchanov
  • L. V. Stepakova
  • G. L. Starova
  • R. R. Kostikov
Article

Abstract

1-Methyl-2-(2-methylpropenylidene)-1-phenylcyclopropane, 7-(2-methylpropenylidene)bicyclo[4.1.0]heptane, and (Z)-9-(2-methylpropenylidene)bicyclo[6.1.0]non-4-ene react with N-benzylideneanilines in the presence of boron trifluoride-ether complex to give pyrrolidine derivatives. Reactions of 1-methyl-1-phenyl-2-diphenylvinylidenecyclopropane with N-benzylideneanilines in the presence of BF3·Et2O, Yb(OTf)3, or Sc(OTf)3 lead to the formation of substituted 1,2,3,4-tetrahydroquinolines. 7-Diphenylvinylidenebicyclo[4.1.0]heptane in the presence of BF3·Et2O undergoes isomerization into 5-phenyl-8,9,10,11-tetrahydro-7H-cyclohepta[a]naphthalene.

Keywords

Schiff Base Colorless Crystal Boron Trifluoride Anhydrous Methylene Chloride Allyl Rearrangement 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Pleiades Publishing, Ltd. 2007

Authors and Affiliations

  • A. V. Stepakov
    • 1
  • A. G. Larina
    • 1
  • A. P. Molchanov
    • 1
  • L. V. Stepakova
    • 1
  • G. L. Starova
    • 1
  • R. R. Kostikov
    • 1
  1. 1.St. Petersburg State UniversitySt. PetersburgRussia

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