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Lewis Acid Promoted Reactions of 1,1-Diarylallenes and Ketone Derivatives: Synthesis of Indenes by an Addition/Cyclization Reaction

  作者 YAMAZAKI SHOKO; FUKUSHIMA YUGO; UKAI TETSUMA; TATSUMI KOHEI; OGAWA AKIYA  
  选自 期刊  Synthesis;  卷期  2012年44-14;  页码  2155-2161  
  关联知识点  
 

[摘要]The Lewis acid promoted reaction of 1,1-diarylallenes with ketone derivatives was examined. The tin(IV) chloride promoted reaction of diarylallenes with vinyl ketones gave indene derivatives through a conjugate addition/cyclization reaction. The reaction of diphenylallene with diethyl oxomalonate in the presence of one equivalent of tin(IV) chloride at -40 degrees C gave diethyl hydroxy(3-phenyl-1H-inden-2-yl)malonate as the major product through a carbonyl addition/cyclization reaction, whereas the same reactants in the presence of 0.2 equivalents of tin(IV) chloride at 80 degrees C gave diethyl (3-phenyl-1H-inden-2-yl) malonate. Diethyl hydroxy(3-phenyl-1H-inden-2-yl)malonate was also converted into the latter product on heating at 80 degrees C in the presence of 0.2 equivalents of tin(IV) chloride.

 
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