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

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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

DOI: http://dx.doi.org/10.1134/S1070428007010034

Publication date: 2007-01-01