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Synlett 1996; 1996(9): 919-921
DOI: 10.1055/s-1996-5621
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The Effect of Substituents on the Feasibility of [1,3]-Proton Shift Reaction: New Synthetic Opportunities

Vadim A. Soloshonok* , Taizo Ono
  • *National Industrial Research Institute of Nagoya, Hirate-cho 1-1, Kita-ku, Nagoya City, Aichi Pref. 462, Japan, E-mail: solo@nirin.go.jp
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Publication Date:
31 December 2000 (online)

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The effect of substituents on the feasibility of biomimetic [1,3]-proton shift isomerization of the imines derived from benzyl trifluoromethyl ketone has been studied. Reaction rate was shown to be controlled by the nature of substitution on the N-site of starting imine. Specifically, the electron-withdrawing substituent on the phenyl of N-benzyl group facilitates the azomethine-azomethine isomerization.

biomimetic [1,3]-proton shift isomerization