A Theoretical Study of Aromatic Claisen rearrangements

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  • 芳香族化合物のクライゼン転位反応に関する理論的研究
  • 芳香族化合物のクライゼン転移反応に関する理論的研究
  • ホウコウゾク カゴウブツ ノ クライゼン テンイ ハンノウ ニ カンスル リロンテキ ケンキュウ

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Claisen rearrangement reactions are used for one of latent epoxy curing systems. In this work, the reaction mechanism and substituent effects for aromatic Claisen rearrangements are investigated by molecular orbital method in order to control those latent epoxy curing systems. A reaction for allyl phenyl ether is examined. First, on the allyl group rearrangement, a chair-type transition state is generated. From the intermediate detected, in the second step, a hydrogen atom is moved intermolecularly to form the product, o-allyl phenol. The N-allylaniline reaction is found to be less favorable than the allyl phenyl ether reaction, both kinetically and thermodynamically. For condensed-ring allyl ether compounds, it is supposed that more intensive orbital interaction between the condensed-rings and the allyl group gives a smaller activation energy.

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