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The oxidative conversion of (e)-¿-(ary1methylene)-benzeneacetates into substituted phenanthrenes: The propitious use of boron trifluoride with vanadium trifluoride oxide

Journal Article


Abstract


  • Vanadium trifluoride oxide (VOF3)/boron trifluoride diethyl etherate is especially useful for effecting the cyclization of the (E)-α-(arylmethy1ene)benzeneacetates (4a, b, d) to the substituted phenanthrenes (5a, b, d). The products are obtained in 20% higher yield and under milder conditions than by employing the vanadium reagent with trifluoroacetic acid. A survey of the derivatives (4a-n) has shown that oxygen functionality is necessary at the 3- and 4- and/or the 3'- and 4'-positions of (4) for cyclization to occur. © 1984 ASEG.

Publication Date


  • 1984

Citation


  • Halton, B., Maidment, A. I., Officer, D. L., & Warnes, J. M. (1984). The oxidative conversion of (e)-¿-(ary1methylene)-benzeneacetates into substituted phenanthrenes: The propitious use of boron trifluoride with vanadium trifluoride oxide. Australian Journal of Chemistry, 37(10), 2119-2128. doi:10.1071/CH9842119

Scopus Eid


  • 2-s2.0-0000534343

Start Page


  • 2119

End Page


  • 2128

Volume


  • 37

Issue


  • 10

Abstract


  • Vanadium trifluoride oxide (VOF3)/boron trifluoride diethyl etherate is especially useful for effecting the cyclization of the (E)-α-(arylmethy1ene)benzeneacetates (4a, b, d) to the substituted phenanthrenes (5a, b, d). The products are obtained in 20% higher yield and under milder conditions than by employing the vanadium reagent with trifluoroacetic acid. A survey of the derivatives (4a-n) has shown that oxygen functionality is necessary at the 3- and 4- and/or the 3'- and 4'-positions of (4) for cyclization to occur. © 1984 ASEG.

Publication Date


  • 1984

Citation


  • Halton, B., Maidment, A. I., Officer, D. L., & Warnes, J. M. (1984). The oxidative conversion of (e)-¿-(ary1methylene)-benzeneacetates into substituted phenanthrenes: The propitious use of boron trifluoride with vanadium trifluoride oxide. Australian Journal of Chemistry, 37(10), 2119-2128. doi:10.1071/CH9842119

Scopus Eid


  • 2-s2.0-0000534343

Start Page


  • 2119

End Page


  • 2128

Volume


  • 37

Issue


  • 10