The Effect of the Substituents on the Claisen Rearrangement of Allyl [o(or p)-Substituted Phenyl] Ethers

  • HAYASHI Takatoshi
    Department of Chemistry, Faculty of Science and Engineering, Ritsumeikan University
  • GOTO Masanobu
    Department of Chemistry, Faculty of Science and Engineering, Ritsumeikan University

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Other Title
  • Claisen転位反応におよぼず置換基の影響
  • Claisen転位反応 I  Claisen転位反応に及ぼす置換基の影響

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Description

The Claisen rearrangement of allyl[o(or p)-substituted phenyl] ethers was carried out, and the effect of ortho substituents on the conversion was compared with that of para isomers. In the case of para substituted compounds, the order of the magnitude of the conversion was found as follows.<BR>Namely, the conversion decreased with increasing the electronegativity of the substituent. But, in the case of ortho substituted compounds, the substituent effect was remarkably different from that of para substituted compounds, and the order was as follows.<BR>From the data of UV, NMR and the dipole moments of these compounds, it was considered that the magnitude of the conversion of ortho substituted compounds was mainly influenced by the intramolecular mutual repulsion of the dipole between the ether oxygen and the substituent.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1977 (10), 1512-1517, 1977-10-10

    The Chemical Society of Japan

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