Reaction of vinylidenecyclopropanes with aromatic imines in the presence of Lewis acids
Authors: Stepakov, A.; Larina, A.; Molchanov, A.; Stepakova, L.; Starova, G.; Kostikov, R.
Source: Russian Journal of Organic Chemistry, Volume 43, Number 1, January 2007 , pp. 40-49(10)
Publisher: MAIK Nauka/Interperiodica
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.
Document Type: Research article
Publication date: 2007-01-01