Substituent Effect on Claisen Rearrangement of 1-Substituted 2-Cinnamyloxybenzenes.

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  • OKADA Yutaka
    Department of Applied Chemistry, Faculty of Science and Engineering, Ritsumeikan University
  • ADACHI Motoyuki
    Department of Applied Chemistry, Faculty of Science and Engineering, Ritsumeikan University
  • HAYASHI Takatoshi
    Department of Applied Chemistry, Faculty of Science and Engineering, Ritsumeikan University

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  • Substiment Effect on Claisen Rearrangement of 1 Substituted 2 Cinnamyloxybenzenes

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Abstract

Claisen rearrangement of 1-substituted 2-cinnamyloxybenzenes was carried out in decalin. For methyl-, acetyl- and methoxycarbonyl derivatives, the para-rearranged product was predominant. Reactions of nitro- and carboxyl derivatives were relatively fast and produced ortho-rearranged products. For other derivatives, intramolecular hydrogen bonds formed so that keto-enol tautomerism between the ortho-dienone intermediate and ortho-rearranged product proceeded smoothly.

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