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A Comparison of the Photosensitized Rearrangement and the Lewis-Acid-Catalyzed Rearrangement of Spirooxindole Epoxides

  作者 WANG LIHONG; SU YIBING; XU XINMIN; ZHANG WEI  
  选自 期刊  European Journal of Organic Chemistry;  卷期  2012年-33;  页码  6606-6611  
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[摘要]Spirooxindole epoxides undergo smooth rearrangement either under photosensitization conditions or under Lewis acid catalysis to give different products. The photosensitized rearrangement of spirooxindole epoxides leads to 3-acyl-2-indolones, such as spiro[cycloalkane-1,3'-indolin]-2,2'-diones, by cleavage of the CaO bond followed by alkyl migration. The SnCl4-catalyzed rearrangement of spirooxindole epoxides gives 4,4-dialkylquinolin-2,3-diones, such as spiro[cycloalkane-1,4'-quinolin]-2',3'-diones, by cleavage of the C beta O bond followed by aryl migration.

 
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