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Preparation and Rearrangement of N-Vinyl Nitrones: Synthesis of Spiroisoxazolines and Fluorene-Tethered Isoxazoles

  作者 MO DONGLIANG; WINK DONALD A; ANDERSON LAURA L  
  选自 期刊  Organic Letters;  卷期  2012年14-20;  页码  5180-5183  
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[摘要]N-Vinyl nitrones derived from fluorenone have been prepared via a copper-mediated coupling between fluorenone oxime and vinyl boronic acids. These compounds undergo subsequent rearrangement and addition reactions that are distinct from the traditional [3 + 2] cycloaddition reactivity of nitrones. Thermal rearrangements of fluorenone N-vinyl nitrones give spiroisoxazolines, while treatment with alkynes provides fluorene-tethered isoxazoles. The scope and limitations of the preparation of fluorenone N-vinyl nitrones and their subsequent rearrangement and addition reactions are discussed.

 
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