分子内環化複素環合成におけるヘテロ元素の効果

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  • The effects of heteroatoms on the syntheses of heterocycles by intramolecular cyclization.
  • ブンシナイ カンカ フクソカン ゴウセイ ニ オケル ヘテロ ゲンソ ノ コウ

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Solvolysis of vinyl halides affords vinyl cations which also obtained by photolysis via vinyl radicals.<BR>These intermediates react with the nucleophile (O, S, N, or Aryl group) or radical trapping atom which is located in the suitable position in the molecule, producing 5-, 6-, and 7-membered heterocycles.<BR>We have studied the reaction mechanisms in order to establish the new syntheses of heterocycles.<BR>When the heteroatom was oxygen, 5-, 6-, and 7-membered heterocycles were obtained via vinyl cation. On the other hand, sulfur analogues always gave 5- membered heterocycles via both vinyl cation and radical intermediates. These different reactions can be rationalized in terms of the nature of heterocatom and the group bonded to the heteroatom.<BR>Vinyl cations, which were produced by electrophilic addition of acethylenes also reacted by the same manner.<BR>Thus new syntheses of heterocycles were found and the new chemistry of heteroatoms was established.

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