New Development of Ammonium Ylide Chemistry

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Other Title
  • アンモニウムイリド化学の新展開
  • アンモニウムイリド カガク ノ シン テンカイ

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Description

Benzylammonium N-alkylides were generated by reaction of N-[1-(trimethylsilyl) alkyl] benzylammonium salts with cesium fluoride in DMF or HMPA, and their rearrangement products were investigated. [2, 3] Sigmatropic rearrangement of the ylides initially occurred to give isotoluene derivatives and then they were transformed into Sommelet-Hauser rearrangement products and/or Stevens products. The isotoluenes having bicyclic structures were stable at room temperature and aromatized with the aid of a base. The relationship between the configuration of cyclic ammonium ylides and the rearrangement paths is described.

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 114 (11), 880-887, 1994

    The Pharmaceutical Society of Japan

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